Bicyclic amino derivatives and PGD2 antagonist containing the same

ABSTRACT

A compound of the formula (I):                    
     wherein                    
     for example, a compound below:                    
     wherein 
     R 1  is CH 3 , H or Na; and X1-X2-X3 is                    
     or its salt or a hydrate thereof is useful as PGD 2  antagonist and can be used as a drug for treating diseases in which mast cell dysfunction is involved, for example, systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and as an anti-inflammatory agent. It is particularly useful in the treatment of nasal occlusion.

FIELD OF THE INVENTION

The present invention relates to bicyclic amino derivatives and prostaglandin D₂ (hereinafter, referred to as PGD₂) antagonist containing them.

BACKGROUND OF THE INVENTION

Some of bicyclic amino derivatives of the present invention have known to be useful as thromboxane A₂ (TXA₂) antagonists (Japanese Patent Publication (KOKOKU) No. 79060/1993). However, the Japanese Patent Publication (KOKOKU) No. 79060/1993 only describes that the compounds are useful as TXA₂ antagonist, and does not suggest the usefulness thereof as PGD₂ antagonist as disclosed by the present invention.

Namely, the TXA₂ is known to have activities such as action against platelet agglutination, thrombogenesis, etc. The TXA₂ antagonist has therefore been considered to be useful as anti-thrombotic agent, and also in the treatment of myocardial infarction or asthma by antagonizing against TXA₂.

On the other hand, the PGD₂ antagonist of the present invention is useful in the improvement of conditions due to excessive production of PGD₂. Specifically, it is useful as a drug for treating diseases in which mast cell dysfunction is involved, for example, systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and inflammation.

As is apparent from the above, the TXA₂ antagonist and the PGD₂ antagonist are completely different from each other in terms of the active site, mechanism of action, and application, and have quite different characteristics. Accordingly, it has never been expected that any compound could possess these activities simultaneously.

PGD₂ is produced through PGG₂ and PGH₂ from arachidonic acid by the action of cyclooxygenase activated by immunological or unimmunological stimulation and is the major prostanoid that is produced and released from mast cells. PGD₂ has various potent physiological and pathological activities. For example, PGD₂ can cause strong tracheal contraction, which leads to bronchial asthma, and, in a systemic allergic state, it can dilate the peripheral vessels, which leads to an anaphylactic shock. Especially, much attention has been paid on the idea that PGD₂ is one of the causal substances responsible to the onset of nasal occlusion in the allergic rhinitis. Therefore, it has been proposed to develop an inhibitor against the biosynthesis of PGD₂ or an antagonist of PGD₂ receptor as a drug for the reduction of nasal occlusion. However, the inhibitor of PGD₂ biosynthesis possibly affects greatly the synthesis of prostaglandins in other organisms, and therefore, it is desirable to develop an antagonist (blocker) specific to PGD₂ receptor.

DISCLOSURE OF THE INVENTION

The present inventors have studied intensively to develop PGD₂ receptor antagonists (blockers) specific to PGD₂ receptor, and found that compounds of the formula (I) below or its salt possess a potent activity as PGD₂ receptor antagonist, and are chemically and biochemically stable.

Accordingly, the present invention provides a PGD₂ antagonist which comprises a compound of the general formula (I) below or its salt or a hydrate thereof as an active ingredient:

wherein

A is alkylene which optionally is intervened by hetero atom or phenylene, contains oxo group, and/or has an unsaturated bond;

B is hydrogen, alkyl, aralkyl or acyl;

R is COOR₁, CH₂OR₂ or CON(R₃)R₄;

R₁ is hydrogen or alkyl;

R₂ is hydrogen or alkyl;

R₃ and R₄ each are independently hydrogen, alkyl, hydroxy or alkylsulfonyl;

X₁ is a single bond, phenylene, naphtylene, thiophenediyl, indolediyl, or oxazolediyl;

X₂ is a single bond, —N═N—, —N═CH—, —CH═N—, —CH═N—N—, —CH═N—O—, —C═NNHCSNH—, —C═NNHCONH—, —CH═CH—, —CH(OH)—, —C(Cl)═C(Cl)—, —(CH₂)N—, ethynylene, —N(R₅)—, —N(R₅₁)CO—, —N(R₅₂)SO₂—, —N(R₅₃)CON(R₅₄)—, —CON(R₅₅)——SO₂N(R₅₆)—, —O—, —S—, —SO—, —SO₂—, —CO—, oxadiazolediyl, thiadiazolediyl or tetrazolediyl; X₃ is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic group, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, —CH═NR₆ or —N═C(R₇)R₈;

R₅, R₅₁, R₅₂, R₅₃, R₅₄, R₅₅ and R₅₆ each are hydrogen or alkyl; R₆ is hydrogen, alkyl, hydroxy, alkoxy, carbamoyloxy, thiocarbamoyloxy, ureido or thioureido;

R₇ and R₈ each are independently alkyl, alkoxy or aryl;

n is 1 or 2;

Z is —SO₂— or —CO—; and

m is 0 or 1;

wherein a cyclic substituent may has one to three substituents selected from the group consisting of nitro, alkoxy, sulfamoyl, substituted- or unsubstituted-amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, trifluoromethyl, alkylthio, —N═PPh₃, oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy.

THE BEST EMBODIMENT FOR PRACTICING THE INVENTION

Specific examples of compounds usable as a PGD₂ antagonist above include a compound of the formula (I) wherein

m is 0; and when Z is SO₂, both X₁ and X₂ are a single bond; X₃ is alkyl, phenyl, naphthyl, stylyl, quinolyl or thienyl; and a cyclic substituent among these substituents optionally has one to three substituents selected from a group consisting of nitro, alkoxy, substituted- or unsubstituted-amino, halogen, alkyl and hydroxyalkyl, or its salt or hydrate thereof.

Similarly, specific examples include a compound of the formula (I) wherein

when m is 1, both X₁ and X₂ are a single bond; and X₃ is phenyl optionally substituted with halogen, or its salt or hydrate thereof.

Similarly, specific examples include a compound of the formula (I) wherein

when m is 1, X₁ is phenyl, X₂ is —CH₂— or —N═N— and X₃ is phenyl, or its salt or hydrate thereof.

Similarly, examples of compounds of the formula (I) include those of the formula (Ia):

wherein A, B, R, X₁, X₂ and X₃ are as defined above, or its salt or hydrate thereof, provided that those wherein (1) X₁ and X₂ are a single bond, and X₃ is substituted- or unsubstituted-phenyl, or naphthyl; and (2) A is 5-heptenylene, R is COOR₁ (R₁ is hydrogen or methyl), X, is 1,4-phenylene, X₂ is a single bond, and X₃ is phenyl are excluded.

Similarly, examples of compounds of the formula (I) include those of the formula (Ib):

wherein

A, B, R, X₁, X₂ and X₃ are as defined above, or its salt or hydrate thereof, provided that those wherein X₁ and X₂ are a single bond, and X₃ is phenyl, and wherein X₁ is a single bond, X₂ is —O—, and X₃ is benzyl are excluded.

More specifically, examples of compounds of the formula (I) include those of the formula (Ia) wherein X₁ and X₂ are a single bond, X₃ is isoxazolyl, thiadiazolyl, isothiazolyl, morpholyl, indolyl, benzofuryl, dibenzofuryl, dibenzodioxinyl, benzothienyl, dibenzothienyl, carbazolyl, xanthenyl, phenanthridinyl, dibenzoxepinyl, dibenzothiepinyl, cinnolyl, chromenyl, benzimidazolyl or dihydrobenzothiepinyl, or its salt or hydrate thereof.

Similarly, examples of compounds of the formula (I) include those of the formula (Ia) wherein X₁ is a single bond, X₂ is phenylene, X₃ is alkenyl, alkynyl, —CH═NR₆ or —N═C(R₇)R₈, or its salt or hydrate thereof.

Similarly, examples of compounds of the formula (I) include those of the formula (Ia) wherein R is COOR₁, X₁ is phenylene or thiophenediyl, X₂ is a single bond, —N═N—, —CH═CH—, —CONH—, —NHCO— or ethynylene and X₃ is phenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl or thienyl, or its salt or hydrate thereof.

More specifically, examples of the compound (I) of the present invention include those of the formula (Ib) wherein

or its salt or hydrate thereof. Examples of more preferred compounds include those of the formula (Ib) wherein R is COOR₁ (R₁ is as defined above) or its salt or hydrate thereof.

Similarly, examples of compound (I) include those of the formula (Ib) wherein X₁ is phenylene or thiophenediyl, X₂ is a single bond, —N═N—, —CH═CH—, ethynylene, —O—, —S—, —CO—, —CON(R₅₅)— (R₅₅ is as defined above), —N(R₅₁)CO— (R₅₁ is as defined above) and X₃ is phenyl, or its salt or hydrate thereof.

More specifically, examples of compound (I) include those of the formula (Ib) wherein

or its salt or hydrate thereof. Examples of more preferred embodiment include those wherein B is hydrogen, both X₁ and X₂ are a single bond, X₃ is thienyl, thiazolyl, thiadiazolyl, isothiazolyl, pyrrolyl, pyridyl, benzofuryl, benzimidazolyl, benzothienyl, dibenzofuryl, dibenzothienyl, quinolyl or indolyl or its salt or hydrate thereof. Similarly, examples include those wherein X₁ is phenylene, thiophenediyl, indolediyl or oxazolediyl, X₂ is a single bond, —N═N—, —CH═CH—, ethynylene, —S— or —O—, and X₃ is aryl or heterocyclic group, or its salt or hydrate thereof.

The compounds of the general formula (Ia) and (Ib) are novel compounds synthesized by the present inventors.

The terms used throughout the present specification are as defined below.

The term “alkylene” means C₁-C₉ straight or branched chain alkylene, for example, methylene, methylmethylene, dimethylmethylene, methylethylmethylene, ethylene, trimethylene, tetramethylene, pentamethylene, hexamethylene, heptamethylene, octamethyene, nonamethylene , or the like. The alkylene above can be intervened by a hetero atom(s) (oxygen, sulfur, nitrogen atom, or the like) or phenylene (e.g., 1,4-phenylene, 1,3-phenylene, 1,2-phenylene, or the like), contain an oxo group, and/or have one or more double- or triple-bonds at any positions on the chain. Examples include —(CH₂)₂—O—CH₂—, —(CH₂)₂—O—(CH₂)₂—, —(CH₂)₂—O—(CH₂)₃—, —(CH₂)₂—O—(CH₂)₄—, —(CH₂)₂—O—(CH₂)₅—, —(CH₂)₂—O—(CH₂)₆—, —(CH₂)₂—S—(CH₂)₂—, —(CH₂)₃—S—(CH₂)₂—, —CH₂—S—CH₂—, —CH₂—S—(CH₂)₄—, —CH₂—N(CH₃)—CH₂—, —CH₂—NH—(CH₂)₂—, —(CH₂)₂—N(CH₂CH₃)—(CH₂)₃—, —(CH₂)₂-1,4-phenylene—CH₂—, —(CH₂)₂—O-1,3-phenylene—CH₂—, —(CH₂)₂—O-1,2-phenylene—CH₂—, —(CH₂)₂—O-1,4-phenylene—CH₂—, —CH═CH—S—CH₂-1,4-phenylene—CH₂—, —CH═CH—S-1,3-phenylene—(CH₂)₂—, 2-oxopropylene, 3-oxopentylene, 5-oxohexylene, vinylene, 1-propenylene, 2-propenylene, 1-butenylene, 2-butenylene, 3-butenylene, 1,2-butadienylene, 1,3-butadienylene, 1-pentenylene, 2-pentenylene, 3-pentenylene, 4-pentenylene, 1,2-pentadienylene, 1,3-pentadienylene, 1,4-pentadienylene, 2,3-pentadienylene, 2,4-pentadienylene, 1-hexyenylene, 2-hexenylene, 3-hexenylene, 4-hexenylene, 5-hexenylene, 1,2-hexadienylene, 1,3-hexadienylene 1,4-hexadienylene, 1,5-hexadienylene, 2,3-hexadienylene, 2,4-hexadienylene 2,5-hexadienylene, 3,4-hexadienylene, 3,5-hexadienylene, 4,5-hexadienylen, 1,1-dimethyl-4-hexenylen, 1-heptenylene, 2-heptenylene, 3-heptenylene, 4-heptenylene, 5-heptenylene, 2,2-dimethyl-5-heptenylene, 6-heptenylene, 1,2-heptadienylne, 1,3-heptadienylene, 1,4-heptadienylene, 1,5-heptadienylene, 1,6-heptadienylene, 2,3-heptadienylene, 2,4-heptadienylene, 2,5-heptadienylene, 2,6-heptadienylene, 3,4-heptadienylene, 3,5-heptadienylene, 3,6-heptadienylene, 4,5-heptadienylene, 4,6-heptadienylene or 5,6-heptadienylene, 1-propynylene, 3-butynylene, 2-pentynylene, 5-hexynylene, 6-heptynylene, —(CH₂)—CH═CH—O—(CH₂)₂—,—CH₂—S—(CH₂)₃——CH₂—cis-CH═CH-1,2-phenylene-CH₂—, —CH═CH-1,4-phenylene-(CH₂)₂—, -4-oxo-4,5-hexenylene-, and the like.

The term “alkyl” means C₁-C₂₀ straight or branched chain alkyl, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, n-pentyl, i-pentyl, neopentyl, t-pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, tridecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, nonadecyl, icosyl, and the like.

The term “aryl” means C₆-C₁₄monocyclic or condensed ring, for example, phenyl, naphthyl (e.g., 1-naphthyl, 2-naphtyl), anthryl (e.g., 1-anthryl, 2-anthryl, 9-anthryl), phenanthryl (e.g., 2-phenanthryl, 3-phenanthryl, 9-phenanthryl), fluorenyl (e.g., 2-fluorenyl), and the like. Phenyl is especially preferred.

The term “aralkyl” means a group formed by substituting an alkyl as defined above with an aryl above at any substitutable positions on the alkyl. Examples include benzyl, phenethyl, phenylpropyl (e.g., 3-phenylpropyl), naphtylmethyl (e.g., α-naphtylmethyl), anthrylmethyl (e.g., 9-anthrylmethy), phenanthrylmethyl (e.g., 3-phenanthrylmethyl), and the like.

The term “acyl” means C₁-C₉ acyl derived from aliphatic carboxylic acid, for example, formyl, acetyl, propionyl, butyryl, valeryl, and the like.

The term “alkylsulfonyl” means a group formed by substituting a sulfonyl with an alkyl above, for example, methylsulfonyl, ethylsulfonyl, propylsulfonyl, and the like.

The term “alkenyl” is C₂-C₂₀ straight or branched chain alkenyl, which corresponds to an alkyl above containing one or more double bonds. Examples include vinyl, 1-propenyl, 2-propenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1,2-butadienyl, 1-pentenyl, 1,2-pentadienyl, 2-hexyenyl, 1,2-hexadienyl, 3-heptenyl, 1,5-heptadienyl, and the like.

The term “alkynyl” is C₂-C₂₀ straight or branched chain, alkynyl, which corresponds to an alkyl above containing one or more triple bonds. Examples include ethynyl, 1-propynyl, 2-propynyl, 1-butynyl, 2-butynyl, 3-butynyl, and the like.

The term “heterocyclic group” means 5-7 membered cyclic group containing one or more hetero atoms selected independently from the group consisting of oxygen, sulfur and/or nitrogen atom on the ring, and is optionally condensed with a carbon ring or other heterocyclic group at any substitutable positions. Examples include pyrrolyl (e.g., 1-pyrrolyl, 3-pyrrolyl), indolyl (e.g., 2-indolyl, 3-indolyl, 6-indolyl), carbazolyl (e.g., 2-carbazolyl, 3-carbazolyl), imidazolyl (e.g., 1-imidazolyl, 4-imidazolyl), pyrazolyl (e.g., 1-pyrazolyl, 3-pyrazolyl), benzimidazolyl (e.g., 2-benzimidazolyl, 5-benzimidazolyl), indazolyl (e.g., 3-indazolyl), indolizinyl (e.g., 6-indolyzinyl), pyridyl (e.g., 2-pyridyl, 3-pyridyl, 4-pyridyl), quinolyl (e.g., 8-quinolyl), isoquinolyl (e.g., 3-isoquinolyl), acridyl (e.g., 1-acridyl), phenanthrydinyl (e.g., 2-phenanthrydinyl, 3-phenanthrydinyl), pyridazinyl (e.g., 3-pydidazinyl), pyrimidinyl (e.g., 4-pyrimidinyl), pyrazinyl (e.g., 2-pyrazinyl), cinnolinyl (e.g., 3-cinnolinyl), phthaladinyl (e.g., 5-phthaladinyl), quinazolinyl (e.g., 2-quinazolinyl), isoxazolyl (e.g., 3-isoxazolyl, 4-isoxazolyl), benzisoxazolyl (e.g., 1,2-benzisoxazol-4-yl, 2,1-benzisoxazol-3-yl), oxazolyl (e.g., 2-oxazolyl, 4-oxazolyl, 5-oxazolyl), benzoxazolyl (e.g., 2-benzoxazolyl), benzoxadiazolyl (e.g., 4-benzoxadiazolyl), isothiazolyl (e.g., 3-isothiazolyl, 4-isothiazolyl) benzisothiazolyl (e.g., 1,2-benzisothiazol-3-yl, 2,1-benzisothizol-5-yl), thiazolyl (e.g., 2-thiazolyl), benzothiazolyl (e.g., 2-benzothiazolyl), thiadiazolyl (e.g., 1,2,3-thiadiazol-4-yl), oxadiazolyl (e.g., 1,3,4-oxadiazol-2-yl), dihydroxadiazolyl (e.g., 4,5-dihydro-1,2,4-oxadiazol-3-yl), furyl (e.g., 2-furyl, 3-furyl), benzofuryl (e.g., 3-benzofuryl), isobenzofuryl (e.g., 1-isobenzofuryl), thienyl (e.g., 2-thienyl, 3-thienyl), benzothienyl (1-benzothiophen-2-yl, 2-benzothiophen-1-yl), tetrazolyl (e.g., 5-tetrazolyl), benzodioxolyl (e.g., 1,3-benzodioxol-5-yl), dibenzofuryl (e.g., 2-dibenzofuryl, 3-dibenzofuryl), dibenzoxepinyl (e.g., dibenz[b,f]oxepin-2-yl), dihydrodibenzoxepinyl (e.g., dihydrodibenz[b,f]oxepin-2-yl, chromenyl (e.g., 2H-chromen-3-yl, 4H-chromen-2-yl), dibenzothiepinyl (e.g., dibenzo[b,f]thiepin-3-yl, dihydrodibenzo[b,f]thiepin-3-yl), morpholinyl (e.g., 1,4-morpholin-4-yl), phenothiadinyl (2-phenothiadinyl), cyclopentathienyl (e.g., cyclopenta[b]thiophen-3-yl), cyclohexathienyl (e.g., cyclohexa[b]thiophen-3-yl), cyclohexathienyl (e.g., cyclohexa[b]thiophen-3-yl), cycloheptathienyl (e.g., cyclohepta[b]thiophen-3-yl), dibenzothienyl (e.g., 2-dibenzothienyl), dibenzopyranyl (e.g., 2-dibenzopyranyl), dibenzo-p-dioxyl (e.g., 2-dibenzo-p-dioxyl), and the like.

The term “cycloalkyl” means C₃-C₈ cyclic alkyl, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, and the like.

The term “cycloalkenyl” means C₃-C₈ cyclic alkenyl, for example, cyclopropenyl (e.g., 1-cyclopropenyl), cyclobutenyl (e.g., 2-cyclobuten-1-yl), cyclopentenyl (1-cyclopenten-1-yl), cyclohexenyl (1-cyclohexen-1-yl), and the like.

The term “alkoxy” means C₁-C₆ alkoxy, for example, methoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, and the like.

Examples of the substituted amino in the definition of “substituted- or un-substituted-amino” include mono- or di-substituted amino such as methylamino, ethylamino, dimethylamino, cyclohexylamino, phenylamino, diphenylamino, or cyclic amino such as piperidino, piperadino or morpholino.

The term “acyloxy” means an acyloxy derived from the “acyl” above, for example, acetyloxy, propionyloxy, butyryloxy, valeryloxy, and the like.

The term “halogen” means fluorine, chlorine, bromine and iodine.

The term “alkoxycarbonyl” means an alkoxycarbonyl group derived from the “alkoxy” above, for example, methoxycarbonyl, ethoxycarbonyl, phenyloxycarbonyl, and the like.

The term “aralkyloxycarbonyl” means an aralkyloxycarbonyl group derived from the “aralkyl” above, for example, benzyloxycarbonyl, phenethyloxycarbonyl, and the like.

The term “aryloxycarbonyl” means an aryloxycarbonyl group derived from the “aryl” above, for example, phenyloxycarbonyl, naphtyloxycarbonyl, and the like.

The term “alkenyloxy” means an alkenyloxy group derived from the “alkenyl” above, for example, vinyloxy, 1-propenyloxy, 2-butenyloxy, and the like.

The term “hydroxyalkyl” means a hydroxyalkyl group derived from the “alkyl” above, for example, hydroxymethyl, hydroxyethyl, hydroxypropyl, and the like.

The term “alkylthio” means an alkylthio group derived from the “alkyl” above, for example, methylthio, ethylthio, propylthio, and the like.

The term “alkylenedioxy” means C₁-C₃ alkylenedioxy, for example, methylenedioxy, ethylenedioxty, propylenedioxy, and the like.

In the case of “phenylene, “naphtylene”, “thiophenediyl”, “indolediyl”, “oxazolediyl”, “oxadiazolediyl” and tetrazolediyl”, the said group can bind to the neighboring groups at any two substitutable sites.

In the definitions above, when a substituent(s) is cyclic, it may be substituted by one to three substituents selected from nitro, alkoxy, sulfamoyl, substituted- or un-substituted-amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, trifluoromethyl, alkylthio, —N═PPh₃, oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy. The substituent(s) may bind to any substitutable positions on the ring.

Examples of salts of the compound (I) include those formed with an alkali metal (e.g., lithium, sodium or potassium), an alkali earth metal (e.g., calcium), an organic base (e.g., tromethamine, trimethylamine, triethylamine, 2-aminobutane, t-butylamine, diisopropylethylamine, n-butylmethylamine, cyclohexylamine, dicyclohexylamine, N-isopropylcyclohexylamine, furfurylamine, benzylamine, methylbenzylamine, dibenzylamine, N,N-dimethylbenzylamine, 2-chlorobenzylamine, 4-methoxybenzylamine, 1-naphthylenemethylamine, diphenylbenzylamine, triphenylamine, 1-naphthylamine, 1-aminoanthoracene, 2-aminoanthoracene, dehydroabiethylamine, N-methylmorpholine or pyridine), an amino acid (e.g., lysine, or arginine), and the like.

The term “hydrate” means a hydrate of the compound of the formula (I) or its salt. Examples include mono- and dihydrates.

The present compounds are shown by the formula (I) and are inclusive of the form of any types of stereoisomers (e.g., diastereomer, epimer, enantiomer) and racemic compounds.

Among the compounds of the general formula (I), those wherein m=1, especially, those shown in Tables 3b and 3c below are known compounds described in Japanese Patent Publication (KOKAI) No. 180862/1990.

Among the compounds of the general formula (I), those wherein m=0, [i.e., those shown by the general formula (I′)], can be prepared by reacting an amino compound of the general formula (II) with a reactive derivative of sulfonic acid or carboxylic acid corresponding to the partial structure: Z—X₁—X₂—X₃ as shown below.

Wherein A, B, R, X₁, X₂, X₃, Y and Z are as defined above.

A sulfonic acid corresponding to the partial structure: Z—X₁—X₂—X₃ is a compound of the general formula X₃—X₂—X₁—SO₂OH and a carboxylic acid corresponding to the said partial structure is a compound of the general formula X₃—X₂—X₁—COOH. Reactive derivative of these sulfonic or carboxylic acids means a corresponding halide (e.g., chloride, bromide, iodide), acid anhydride (e.g., mixed acid anhydride with formic acid or acetic acid), active ester (e.g., succinimide ester), and examples thereof generally include acylating agents used for the acylation of amino group. The carboxylic acid X₃—X₂—X₁—COOH can be used in the reaction as it is without converting into a reactive derivative, in the presence of a condensing agent (e.g., dicyclohexylcarbodiimide (DCC), 1-ethyl-3-(3-dimetylaminopropyl)carbodiimide, N,N′-carbonyldiimidazole) which are used in the condensing reaction between amine and carboxylic acid.

The reaction can be conducted under the conditions generally used for the acylation of amino group. For example, in the case of condensation using an acid halide, the reaction is carried out using a solvent such as an ether solvent (e.g., diethylether, tetrahydrofuran, dioxane), benzene solvent (e.g., benzene, toluene, xylene), halogenated hydrocarbon solvent (e.g., dichloromethane, dichloroethane, chloroform), ethyl acetate, dimethylformamide, dimethyl sulfoxide, acetonitrile, or the like, if necessary, in the presence of a base (e.g., organic base such as triethylamine, pyridine, N,N-dimethylaminopyridine, N-methylmorpholine; inorganic base such as sodium hydroxide, potassium hydroxide, potassium carbonate, or the like) undercooling, at room temperature or under heating, preferably at temperature ranging from −20° C. to a temperature under cooling, or from room temperature to a refluxing temperature of the reaction system, for several min to several hr, preferably for 0.5 hr to 24 hr, more preferably, for 1 hr to 12 hr.

The reaction conditions for the reaction between other reactive derivative or a free acid and an amine (II) can be determined in a conventional manner depending on the characteristics of the respective reactive derivative or free acid.

The reaction product can be purified by conventional purification methods, for example, the extraction with a solvent, chromatography, recrystallization, or the like.

Specific examples of the compound (II) as a starting material for the present method are as follows. Examples of 3-amino[2.2.1]bicyclic compound include 7-(3-aminobicyclo[2.2.1]hept-2-yl)-5-heptenoic acid, 7-(3-aminobicyclo[2.2.1]hept-2-yl)-2,2-dimethyl-5-heptenoic acid, 7-(N-metnyl-3-aminobicyclo[2.2.1]hept-2-yl)-5-heptenoic acid, 6-(3-aminobicyclo[2.2.1]hept-2-yl)-5-hexenoic acid. Specific examples of 2-amino-6,6-dimethyl[3.1.1]bicyclic compound include 7-(2-amino-6,6-dimethylbicyclo[3.1.1]hept-3-yl)-5-heptenoic acid. In these starting compounds, the heptenoic acid chain may be saturated to form heptanoic acid chain, intervened by a hetero atom(s) or a hetero group(s) such as —O—, —S—, —NH—, or a phenylene(s), or substituted with an oxo group. Examples of such compounds include 7-(3-aminobicyclo[2.2.1]hept-2-yl)heptanoic acid, 4-[2-(2-aminobicyclo[3.1.1]hept-3-yl)ethoxyphenylacetic acid, 7-(3-aminobicyclo[2.2.1]hept-2-yl)-6-oxo-heptanoic acid. These starting compounds are either described in the Japanese Patent Publication (KOKOKU) No. 79060/1993or23170/1991, or can be prepared according to the method described therein.

Sulfonic acid X₃—X₂—X₁—SO₂OH and carboxylic acid X₃—X₂—X₁—COOH corresponding to the partial structure Z—X₁—X₂—X₃ mean a sulfonic acid or carboxylic acid having substituents corresponding to the Xs above. That is, examples include alkane-sulfonic acid or -carboxylic acid, alkene-sulfonic acid or -carboxylic acid, alkyne-sulfonic acid or -carboxylic acid, cycloalkane-sulfonic acid or -carboxylic acid, cycloalkene-sulfonic acid or -carboxylic acid, aryl-sulfonic acid or -carboxylic acid, aralkyloxy-sulfonic acid or -carboxylic acid, heterocyclic-substituted-sulfonic acid or -carboxylic acid, heteroarylalkyl-sulfonic acid or -carboxylic acid, and substituted-amino-sulfonic acid or -carboxylic acid. Each of sulfonic and carboxylic acids may have a substituent(s) above. These sulfonic acids and carboxylic acids are commercially available or can be easily synthesized from a known compound(s) in accordance with a known method. Upon reaction, the sulfonic or carboxylic acid can be converted into the corresponding reactive derivative above, if necessary. For example, when an acid halide is needed, the compound is reacted with thionyl halide (e.g., thionyl chloride), phosphorous halide (e.g., phosphorous trichloride, phosphorous pentachloride) or oxalyl halide (e.g., oxalyl chloride) in accordance with a known method such as those described in a literature (e.g., Shin-Jikken-Kagaku-Koza, vol. 14, pp. 1787 (1978); Synthesis, 852-854 (1986); Shin-Jikken-Kagaku-Koza, vol. 22, pp. 115 (1992)). The other reactive derivatives can also be prepared in accordance with a known method.

Among the objective compounds (I), those wherein the side chain A contains an unsaturated bond, especially, a double bond, can also be prepared by reacting an aldehyde derivative of the general formula (III) below with an ylide compound corresponding to the rest part of the side chain A-R under the conditions for the Wittig reaction:

wherein A, B, R, X₁, X₂, X₃, Y and Z are as defined above.

The starting compound (III) can be prepared in accordance with a method described in, for example, Japanese Patent Publication (KOKAI) No. 256650/1990. Further, an ylide compound corresponding to the rest part of the side chain A-R can be synthesized by reacting triphenylphosphine with a corresponding halogenated alkanoic acid, or an ester derivative, ether derivative or amide derivative thereof in the presence of a base according to a known method.

Among the objective compounds (I), those wherein R is COOH can be converted into a corresponding ester derivative, alcohol derivative, ether derivative, amide derivative, if desired. For example, ester derivatives can be prepared by esterifying a carboxylic acid in a conventional manner. An ester derivative, when reduced, gives an alcohol derivative, and amidated, gives an amide derivative. An ether derivative can be obtained by O-alkylating an alcohol derivative.

The compound (I) of the present invention shows antagonistic effect against PGD₂ in vitro through the binding to PGD₂ receptor, and is useful as a drug for treating diseases in which mast cell dysfunction due to excessive production of PGD₂ is involved. For example, the compound (I) is useful as a drug for treating diseases, such as systemic mastocytosis and disorder of systemic mast cell activation, and also tracheal contraction, asthma, allergic rhinitis, allergic conjunctivitis, urticaria, injury due to ischemic reperfusion, and inflammation. The compound (I) shows preventive effect on nasal occlusion in vivo, and therefore is especially useful as a drug for treating them.

When using a compound (I) of the present invention in treatment, it can be formulated into ordinary formulations for oral and parenteral administration. A pharmaceutical composition containing a compound (I) of the present invention can be in the form for oral and parenteral administration. Specifically, it can be formulated into formulations for oral administration such as tablets, capsules, granules, powders, syrup, and the like; those for parenteral administration such as injectable solution or suspension for intravenous, intramuscular or subcutaneous injection, inhalant, eye drops, nasal drops, suppositories, or percutaneous formulations such as ointment.

In preparing the formulations, carriers, excipients, solvents, and bases known to one ordinary skilled in the art may be used. In case of tablets, they are prepared by compressing or fomulating an active ingredient together with auxiliary components. Examples of usable auxiliary components include pharmaceutically acceptable excipients such as binders (e.g., cornstarch), fillers (e.g., lactose, microcrystalline cellulose), disintegrants (e.g., starch sodium glycolate) or lubricants (e.g., magnesium stearate). Tablets may be coated appropriately. In the case of liquid formulations such as syrups, solutions, or suspensions, they may contain suspending agents (e.g., methyl cellulose), emulsifiers (e.g., lecithin), preservatives, and the like. In the case of injectable formulations, it may be in the form of solution or suspension, or oily or aqueous emulsion, which may contain suspension-stabilizing agent or dispensing agent, and the like. In the case of an inhalant, it is formulated into a liquid formulation applicable to an inhaler. In the case of eye drops, it is formulated into a solution or a suspension. Especially, in the case of nasal drug for treating nasal occlusion, it can be used as a solution or suspension prepared by a conventional formulating method, or as a powder formulated using a powdering agent (e.g., hydroxypropyl cellulose, carbopole), which are administered into the nasal cavity. Alternatively, it can be used as an aerosol after filling into a special container together with a solvent of low boiling point.

Although an appropriate dosage of the compound (I) varies depending on the administration route, age, body weight, sex, or conditions of the patient, and the kind of drug(s) used together, if any, and should be determined by the physician in the end, in the case of oral administration, the daily dosage can generally be between about 0.01-100 mg, preferably about 0.01-10 mg, more preferably about 0.1-10 mg, per kg body weight. In the case of parenteral administration, the daily dosage can generally be between about 0.001-100 mg, preferably about 0.001-1 mg, more preferably about 0.01-1 mg, per kg body weight. The daily dosage can be administered in 1-4 divisions.

The following Examples are provided to further illustrate the present invention and are not to be construed as limiting the scope thereof.

EXAMPLE 1

Methyl (Z)-7-[(1S,2R,3R,4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (II-1) (251 mg, 1.00 mmol) was dissolved in methylene chloride (8 ml) and triethylamine (0.238 ml, 2.00 mmol) was added thereto under a nitrogen atmosphere. To the mixture was added 2-chlorosulfonyldibenzofuran (350 mg, 1.31 mmol) under ice-cooling, and the mixture was stirred for 30 min and allowed to warm up to room temperature. The reaction mixture was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:4)) and recrystallized from n-hexane (10 ml) to yield methyl (Z)-7-[(1S, 2R, 3R, 4R)-3-(2-dibezofuryl)sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (342 mg, 0.710 mmol). Yield 71%, mp 115-116° C.

Elemental analysis (C₂₇H₃₁NO₅S)

Calcd. (%): C, 67.34; H, 6.49; N, 2.91; S, 6.66

Found (%): C, 67.16; H, 6.47;N, 2.99; S, 6.66

IR (CHCl₃):3382, 3024, 2952, 2874, 1726, 1583, 1465, 1442, 1319, 1245, 1154, 1121, 1104, 1071, 1019, 890, 840, 817/cm.

¹H NMR(CDCl₃)δ: 0.94-1.92(14H, m), 2.15-2.24(3H, m), 2.99-3.07(1H, m), 3.66(3H, s), 4.98(1H, d, J=6.6 Hz), 5.10-5.22(2H, m), 7.39-7.46(1H, m), 7.51-7.70(3H, m), 7.87-8.13(2H, m), 8.53(1H, d, J=2.1 Hz)

[α]_(D)=−0.6° (CHCl₃, c=1.01%,23° C.).

([α]₃₆₅=+37.0° (CHCl₃, c=1.01%, 23° C.).

Methyl (Z)-7-[(1S, 2R, 3R, 4R)-3-(2-dibezofuryl)-sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1a-1) (234 mg, 0.50 mmol) was dissolved in methanol (6 ml)/tetrahydrofuran (4 ml). To the solution was added 1 N potassium hydroxide (1.50 ml, 1.50 mmol) under ice-cooling. After the reaction mixture was warmed up to room temperature, it was allowed to react for 16 hr and concentrated to remove the solvent. To the residue were added ethyl acetate (50 ml) and water (10 ml), and then 1 N HCl (2.00 ml, 2.00 mmol), and the organic layer was separated. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (n-hexane/ethyl acetate (1:1) containing 0.2% acetic acid) to yield (Z)-7-[(1S, 2R, 3R, 4R)-3-(2-dibezofuryl)-sulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1a-2) (203 mg, 0.434 mmol). Yield 87%, oil.

IR (CHCl₃): 3266, 3026, 2952, 2874, 1708, 1465, 1443, 1423, 1319, 1267, 1245, 1153, 1121, 1104, 1072, 906/cm.

¹H NMR(CDCl₃)δ: 0.93-1.94(14H, m), 2.12-2.19(1H, m), 2.26(2H, t, J=7.2 Hz), 3.00-3.08(1H, m), 5.12-5.25(2H, m), 5.26(1H, d, J=6.6 Hz), 7.38-7.45(1H, m), 7.51-7.70(3H, m), 7.87-8.13(2H, m), 8.54(1H, d, J=2.1 Hz).

[α]_(D)=+6.8° (CHCl₃, c=1.08%, 23° C.).

(Z)-7-[(1S, 2R, 3R, 4R)-3-(2-Dibezofuryl)sulfonylamino-bicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1a-2) (453 mg, 0.97 mmol) was dissolved in methanol (5 ml). After addition of 1 N sodium methoxide/methanol (1.034 N, 0.937 ml, 0.97 mmol), the mixture was allowed to warm up to room temperature and to react for 1 hr. The solvent was removed by distillation to yield the sodium salt (1a-3) (457 mg, 0.933 mmol). Yield 96%.

Amorphous powder.

Elemental analysis (C₂₆H₂₈NO₅SNa 0.6H₂O)

Calcd.(%): C, 62.41; H, 5.88; N, 2.80; S, 6.41; Na, 4.59

Found (%): C, 62.45; H, 5.92; N, 2.99; S, 6.49; Na, 4.46

IR (KBr): 434, 3280, 3074, 3007, 2952, 2873, 1566, 1467, 1444, 1417, 1344, 1315, 1270, 1248, 1200, 1189, 1154, 1124, 1107, 1075, 1058, 895, 842, 818/cm.

¹H NMR(CD₃OD)δ: 1.02-2.05(16H, m), 2.16-2.23(1H, m), 2.94-3.00(1H, m), 4.98-5.05(2H, m), 7.41-7.48(1H, m), 7.53-7.62(1H, m), 7.66(1H, d, J=8.4 Hz), 7.77(1H, d, J=8.4 Hz), 8.57(1H, d, J=2.1 Hz).

[α]_(D)=−15.2° (CH₃OH, c=1.07%, 22° C.).

EXAMPLE 2

Methyl (Z)-7-[(1S, 2R, 3R, 4R)-3-aminobicyclo[2.2.1]hept-2-yl]-5-heptenoate trifrluroroacetate (II-2) (232 mg, 0.636 mmol), which was prepared by the method described in Reference Example 4 of the Japanese Patent Publication (KOKOKU) No. 79060/1993, was dissolved in methylene chloride (5 ml). To the solution were added triethylamine (0.279 ml, 2.00 mmol) and 4-biphenylcarbonyl chloride under ice-cooling and stirred for 7 hr at the sametemperature. The reaction mixture was purified by column chromatography on silica gel (ethyl acetate/n-hexane (1:4)) to yield methyl (Z)-7-[(1S, 2R, 3R, 4R)-3-(4-biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate(1k-11)(221 mg, 0.512 mmol). The compound(1k-11) (190 mg, 0.440 mmol)was dissolved in methanol (6 ml). To the solution was added 1 N KOH (1.10 ml, 1.10 mmol) under ice-cooling and stirred for 15 hr at room temperature. The reaction mixture was concentrated in vacuo. The residue, after the addition of water (20 ml) and 1 N HCl (2 ml), was extracted with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by column chromatography on silica gel (ethyl acetate/hexane (1:1) containing 0.3% acetic acid) to yield (Z)-7-[(1S, 2R, 3R, 4R)-3-(4-biphenyl)carbonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoic acid (1k-12) (172 mg, 0.412 mmol). Yield 94%.

The following compounds can also be prepared in the following manner.

EXAMPLE 3

To a suspension of 4-carboxybutyltriphenylphosphonium bromide (14.8 g, 33.3 mmol) and tetrahydrofuran (80 ml) was added potassium t-butyrate (7.55 g, 67.3 mmol) at room temperature under a nitrogen atmosphere. After stirring for 1 hr at room temperature, the mixture was cooled to −20° C. and a solution of N-[(1S, 2S, 3S, 4R)-3-formylmethylbicyclo[2.2.1]hept-2-yl]benzenesulfonamide (III-1) (Japanese Patent Publication (KOKAI) No. 256650/1990, Reference Example 2) (3.25 g, 11.1 mmol) in tetrahydrofuran (20 ml) was added slowly. After stirring for about 1 hr at −20° C., the ice bath was removed and the mixture was further stirred for 1hr. To there action solution was added 2 N HCl and the mixture was extracted with ethyl acetate, washed with water and brine, and concentrated. After the addition of toluene and 1 N sodium hydroxide to the resultant crude product, aqueous layer was separated. The organic layer was washed with water again and the washing was combined with the previously obtained aqueous layer. After the addition of 2 N HCl, the aqueous solution was extracted with ethyl acetate. The extract was washed with water and brine, dried over sodium sulfate, and concentrated. The residue was purified by column chromatography on silica gel to obtain calcium (Z)-7-[(1R, 2S, 3S, 4S)-3-phenylsulfonylaminobicyclo[2.2.1]hept-2-yl]-5-heptenoate (1d-1) (3.29 g, yield 79%, mp 62° C.).

Elemental analysis (C₂₀H₂₇NO₄S)

Calcd.(%): C, 63.63; H, 7.21; N, 3.71; S, 8.49

Found (%): C, 63.56; H, 7.21; N, 3.83; S, 8.43

[α]_(D)=+5.3±0.5° (CHCl₃, c=1.003%, 22° C.)

[α]_(D)=+27.1±0.70° (MeOH, c=1.015% 24° C.)

IR(Nujol) 3282, 3260, 3300, 2400, 1708, 1268, 1248, 1202, 1162, 1153, 1095, 1076/cm.

¹H NMR δ 0.88-2.10(m, 14H), 2.14(br S, 1H), 2.34(t, J=7.2 Hz, 2H), 2.95-3.07(m, 1H), 5.13-5.35(m, 3H), 7.45-7.64(m, 3H), 7.85-7.94(m, 2H), 9.52(brS, 1H).

Compounds prepared in accordance with a method described in Examples above are shown in Tables below.

TABLE 1a No. R₁ X₁—X₂—X₃

1a-1 1a-2 1a-3 CH₃ H Na

1a-4 1a-5 CH₃ H

1a-6 1a-7 CH₃ H

1a-8 1a-9 CH₃ H

1a-10 1a-11 CH₃ H

1a-12 1a-13 CH₃ H

1a-14 1a-15 CH₃ H

1a-16 1a-17 CH₃ H

1a-18 1a-19 CH₃ H

1a-20 1a-21 CH₃ H

1a-22 H

1a-23 H

1a-24 1a-25 1a-26 CH₃ H Na

1a-27 1a-28 1a-29 CH₃ H Na

1a-30 1a-31 CH₃ H

1a-32 1a-33 CH₃ H

1a-34 CH₃

1a-35 1a-36 CH₃ H

1a-37 1a-38 CH₃ H

1a-39 1a-40 CH₃ H

1a-41 H

1a-42 1a-43 CH₃ H

1a-44 1a-45 CH₃ H

1a-46 1a-47 1a-48 CH₃ H Na

1a-49 1a-50 CH₃ H

1a-51 1a-52 CH₃ H

1a-53 1a-54 CH₃ H

1a-55 1a-56 CH₃ H

1a-57 1a-58 CH₃ H

1a-59 1a-60 CH₃ H

1a-61 1a-62 CH₃ H

1a-63 1a-64 CH₃ H

1a-65 1a-66 CH₃ H

1a-67 1a-68 CH₃ H

1a-69 1a-70 CH₃ H

1a-71 1a-72 CH₃ H

1a-73 1a-74 CH₃ H

1a-75 1a-76 CH₃ H

1a-77 1a-78 CH₃ H

1a-79 H

1a-80 1a-81 CH₃ H

1a-82 1a-83 CH₃ H

1a-84 H

1a-85 H

1a-86 H

1a-87 H

1a-88 1a-89 CH₃ H

1a-90 1a-91 CH₃ H

1a-92 1a-93 CH₃ H

1a-94 H

1a-95 H

1a-96 H

1a-97 H

1a-98 1a-99 H Na

1a-100 1a-101 CH₃ H

1a-102 CH₃

1a-103 1a-104 CH₃ H

1a-105 1a-106 CH₃ H

1a-107 1a-108 CH₃ H

1a-109 1a-110 CH₃ H

1a-111 1a-112 CH₃ H

1a-113 1a-114 CH₃ H

1a-115 1a-116 1a-117 1a-118 CH₃ H Na i-Pr

1a-119 1a-120 1a-121 CH₃ Na H

1a-122 1a-123 CH₃ H

1a-124 CH₃

1a-125 1a-126 CH₃ H

1a-127 1a-128 CH₃ H

1a-129 CH₃

1a-130 1a-131 CH₃ H

1a-132 1a-133 CH₃ H

1a-134 H

1a-135 1a-136 CH₃ H

1a-137 1a-138 CH₃ H

1a-139 1a-140 CH₃ H

1a-141 1a-142 CH₃ H

1a-143 H

1a-144 H

1a-145 H

1a-146 H

1a-147 H

1a-148 H

1a-149 H

1a-150 H

1a-151 H

1a-152 H

1a-153 H

1a-154 H

1a-155 H

1a-156 H

1a-157 H

1a-158 H

1a-159 H

1a-160 H

1a-161 H

1a-162 H

1a-163 H

1a-164 H

1a-165 H

1a-166 H

1a-167 H

1a-168 H

1a-169 H

1a-170 H

1a-171 1a-172 CH₃ H

1a-173 H

1a-174 H

1a-175 1a-176 CH₃ H

1a-177 1a-178 CH₃ H

1a-179 1a-180 CH₃ H

1a-181 H

1a-182 1a-183 CH₃ H

1a-184 H

1a-185 H

1a-186 1a-187 CH₃ H

1a-188 1a-189 CH₃ H

1a-190 1a-191 CH₃ H

1a-192 1a-193 CH₃ H

1a-194

1a-195

1a-196

1a-197

1a-198

1a-199

1a-200

1a-201

1a-202

1a-203

1a-204

1a-205

1a-206

1a-207

1a-208

1a-209

1a-210

1a-211

1a-212

1a-213

1a-214

1a-215

1a-216

1a-217

1a-218

1a-219

1a-220

1a-221

1a-222

1a-223

1a-224

1a-225

1a-226

1a-227

1a-228

1a-229

1a-230

1a-231

1a-232

1a-233

1a-234

1a-235

1a-236

1a-237

1a-238

1a-239

1a-240

1a-241

1a-242

1a-243

1a-244

1a-245

1a-246

1a-247

1a-248

1a-249

1a-250

1a-251

1a-252

1a-253

1a-254

1a-255

1a-256

1a-257

1a-258

1a-259

1a-260

1a-261

1a-262

1a-263

1a-264

1a-265

1a-266

1a-267

1a-268

1a-269

1a-270

1a-271

1a-272

1a-273

1a-274

1a-275

1a-276

1a-277

1a-278

1a-279

1a-280

1a-281

1a-282

1a-283

1a-284

1a-285

1a-286

1a-287

1a-288

1a-289

1a-290

1a-291

1a-292

1a-293

1a-294

1a-295

1a-296

1a-297

1a-298

1a-299

1a-300

1a-301

1a-302

1a-303

1a-304

1a-305

TABLE 1b

No. R₁ X₁—X₂—X₃ 1b-1 CH₃

1b-2 CH₃

1b-3 H

1b-4 H

1b-5 H

1b-6 H

1b-7 H

1b-8 H

1b-9 H

1b-10 H

1b-11 H

1b-12 H

1b-13 H

1b-14 H

1b-15 H

TABLE 1c

No. R₁ X₁—X₂—X₃ 1c-1 CH₃

1c-2 CH₃

1c-3 K

1c-4 H

1c-5 H

1c-6 H

1c-7 H

1c-8 H

1c-9 H

1c-10 H

1c-11 H

1c-12 H

TABLE 1d

No. R₃ R₄ X₁—X₂—X₃ 1d-1 H SO₂CH₃

1d-2 1d-3 1d-4 H H H H OH SO₂CH₃

1d-5 H SO₂CH₃

1d-6 H SO₂CH₃

1d-7 H SO₂CH₃

1d-8 H SO₂CH₃

1d-9 H SO₂CH₃

1d-10 H SO₂CH₃

1d-11 H SO₂CH₃

1d-12 H SO₂CH₃

1d-13 H SO₂CH₃

1d-14 H SO₂CH₃

1d-15 H SO₂CH₃

TABLE 1e

No. R₁ X₁—X₂—X₃ 1e-1 H

1e-2 H

1e-3 H

1e-4 H

1e-5 H

1e-6 H

1e-7 H

1e-8 H

1e-9 H

1e-10 H

TABLE 1f

No. R₂ X₁—X₂—X₃ 1f-1 H

1f-2 H

1f-3 H

1f-4 H

1f-5 H

1f-6 H

1f-7 H

1f-8 H

1f-9 H

1f-10 H

TABLE 1g

No. R₁ X₁—X₂—X₃ 1g-1 H

1g-2 H

1g-3 H

1g-4 H

1g-5 H

1g-6 H

1g-7 H

1g-8 H

1g-9 H

1g-10 H

1g-11 H

TABLE 1h

No. R₁ X₁—X₂—X₃ 1h-1 H

1h-2 H

1h-3 H

1h-4 H

1h-5 H

1h-6 H

1h-7 H

1b-8 H

1h-9 H

1h-10 H

TABLE 1i

No. R₂ X₁—X₂—X₃ 1i-1 H

1i-2 H

1i-3 H

1i-4 H

1i-5 H

1i-6 H

1i-7 H

1i-8 H

1i-9 H

1i-10 H

1i-11 H

1i-12 H

TABLE 1j

No. R₁ X₁—X₂—X₃ 1j-1 1j-2 1j-3 CH₃ H Na

1j-4 1j-5 H CH₃

1j-6 1j-7 CH₃ H

1j-8 CH₃

1j-9 1j-10 CH₃ H

1j-11 1j-12 CH₃ H

1j-13 1j-14 CH₃ H

1j-15 1j-16 CH₃ H

1j-17 H

1j-18 1j-19 CH₃ H

1j-20 1j-21 CH₃ H

1j-22 H

1j-23 1j-24 CH₃ H

1j-25 1j-26 CH₃ H

1j-27 H

1j-28 1j-29 CH₃ H

1j-30 H

1j-31 H

1j-32 H

1j-33 H

1j-34 H

1j-35 H

1j-36 H

1j-37 H

1j-38 H

TABLE 1k

No. R₁ X₁—X₂—X₃ 1k-1 H

1k-2 1k-3 CH₃ H

1k-4 H

1k-5 H

1k-6 H

1k-7 H

1k-8 H

1k-9 H

1k-10 H

1k-11 CH₃

1k-12 H

1k-13 H

1k-14 H

1k-15 H

1k-16 H

1k-17 H

1k-18 H

1k-19 H

1k-20 H

TABLE 1m

No. R₁ X₁-X₂-X₃ 1m-1 1m-2 CH₃ H

1m-3 1m-4 CH₃ H

1m-5 1m-6 CH₃ H

1m-7 1m-8 CH₃ H

1m-9 1m-10 CH₃ H

1m-11 1m-12 CH₃ H

1m-13 1m-14 CH₃ H

1m-15 1m-16 CH₃ H

1m-17 1m-18 CH₃ H

1m-19 1m-20 CH₃ H

1m-21 H

1m-22 H

1m-23 1m-24 CH₃ H

1m-25 1m-26 CH₃ H

1m-27 1m-28 CH₃ H

1m-29 1m-30 CH₃ H

1m-31 H

1m-32 H

1m-33 H

1m-34 H

1m-35 H

1m-36 H

1m-37 H

1m-38 H

1m-39 H

1m-40 H

TABLE 2a

No. R₁ X₁-X₂-X₃ 2a-1 2a-2 CH₃ H

2a-3 2a-4 2a-5 CH₃ H Na

2a-6 2a-7 CH₃ H

2a-8 2a-9 CH₃ H

2a-10 2a-11 CH₃ H

2a-12 2a-13 CH₃ H

2a-14 2a-15 CH₃ H

2a-16 2a-17 CH₃ H

2a-18 2a-19 CH₃ H

2a-20 2a-21 2a-22 CH₃ H Na

2a-23 2a-24 CH₃ H

2a-25 2a-26 CH₃ H

2a-27 2a-28 CH₃ H

2a-29 2a-30 CH₃ H

2a-31 CH₃

2a-32 2a-33 CH₃ H

2a-34 2a-35 CH₃ H

2a-36 2a-37 CH₃ H

2a-38 2a-39 CH₃ H

2a-40 2a-41 CH₃ H

2a-42 2a-43 CH₃ H

2a-44 2a-45 CH₃ H

2a-46 2a-47 CH₃ H

2a-48 2a-49 CH₃ H

2a-50 2a-51 CH₃ H

2a-52 2a-53 CH₃ H

2a-54 2a-55 CH₃ H

2a-56 2a-57 CH₃ H

2a-58 2a-59 CH₃ H

2a-60 2a-61 CH₃ H

2a-62 2a-63 CH₃ H

2a-64 2a-65 CH₃ H

2a-66 2a-67 CH₃ H

2a-68 2a-69 CH₃ H

2a-70 2a-71 CH₃ H

2a-72 2a-73 CH₃ H

2a-74 2a-75 CH₃ H

2a-76 2a-77 CH₃ H

2a-78 2a-79 CH₃ H

2a-80 2a-81 CH₃ H

2a-82 2a-83 CH₃ H

2a-84 2a-85 CH₃ H

2a-86 2a-87 CH₃ H

2a-88 2a-89 CH₃ H

2a-90 2a-91 CH₃ H

2a-92 2a-93 CH₃ H

2a-94 2a-95 2a-96 2a-97 CH₃ H Na Ca^(½)

2a-98 2a-99 CH₃ H

2a-100 2a-101 CH₃ H

2a-102 2a-103 CH₃ H

2a-104 2a-105 CH₃ H

2a-106 2a-107 CH₃ H

2a-108 2a-109 2a-110 CH₃ H Na

2a-111 2a-112 CH₃ H

2a-113 2a-114 CH₃ H

2a-115 2a-116 CH₃ H

2a-117 2a-118 CH₃ H

2a-119 H

2a-120 H

2a-121 H

2a-122 H

2a-123 H

2a-124 H

2a-125 H

2a-126 H

2a-127 H

2a-128 H

2a-129 H

2a-130 H

2a-131 H

2a-132 H

2a-133 H

2a-134 H

2a-135 H

2a-136 H

2a-137 H

2a-138 H

2a-139 H

2a-140 H

2a-141 H

2a-142 H

2a-143 H

2a-144 H

2a-145 H

2a-146 H

2a-147 H

2a-148 H

2a-149 H

2a-150 H

2a-151 H

2a-152 H

2a-153 H

2a-154 H

2a-155 H

2a-156 H

2a-157 H

2a-158 H

2a-159 H

2a-160 H

2a-161 H

2a-162 H

2a-163 H

2a-164 H

2a-165 H

2a-166 H

2a-167 H

2a-168 H

2a-169 H

2a-170 H

2a-171 H

2a-172 H

2a-173 H

2a-174 H

2a-175 H

2a-176 H

2a-177 H

2a-178 H

2a-179 H

2a-180 H

2a-181 H

2a-182 H

2a-183 H

2a-184 H

2a-185 H

2a-186 H

2a-187 H

2a-188 H

2a-189 H

2a-190 H

2a-191 H

2a-192 H

2a-193 H

2a-194 H

2a-195 H

2a-196 H

2a-197 H

2a-198 H

2a-199 H

2a-200 H

2a-201 H

2a-202 H

2a-203 H

No. X₁-X₂-X₃ 2a-204

2a-205

2a-206

2a-207

2a-208

2a-209

2a-210

2a-211

2a-212

2a-213

2a-214

2a-215

2a-216

2a-217

2a-218

2a-219

2a-220

2a-221

2a-222

2a-223

2a-224

2a-225

2a-226

2a-227

2a-228

2a-229

2a-230

2a-231

2a-232

2a-233

2a-234

2a-235

2a-236

2a-237

2a-238

2a-239

2a-240

2a-241

2a-242

2a-243

2a-244

2a-245

2a-246

2a-247

2a-248

2a-249

2a-250

2a-251

2a-252

2a-253

2a-254

2a-255

2a-256

2a-257

2a-258

2a-259

2a-260

2a-261

2a-262

2a-263

2a-264

2a-265

2a-266

2a-267

2a-268

2a-269

2a-270

2a-271

2a-272

2a-273

2a-274

2a-275

2a-276

2a-277

2a-278

2a-279

2a-280

2a-281

2a-282

2a-283

2a-284

2a-285

2a-286

2a-287

2a-288

2a-289

2a-290

2a-291

2a-292

2a-293

2a-294

2a-295

2a-296

2a-297

2a-298

2a-299

2a-300

2a-301

2a-302

2a-303

2a-304

2a-305

2a-306

2a-307

2a-308

2a-309

2a-310

2a-311

2a-312

2a-313

2a-314

2a-315

TABLE 2b

No. R₁ X₁—X₂—X₃ 2b-1 H

2b-2 H

TABLE 2c

No. R₁ X₁—X₂—X₃ 2c-1 H

2c-2 H

2c-3 H

TABLE 2d

No. R₁ X₁—X₂—X₃ 2d-1 H

2d-2 H

2d-3 H

TABLE 2e

No. R₁ X₂—X₂—X₃ 2e-1 H

2e-2 H

2e-3 H

TABLE 2f

No. R₁ X₁—X₂—X₃ 2f-1 H

2f-2 H

2f-3 H

TABLE 2g

No. R₃ R₄ X₁—X₂—X₃ 2g-1 H SO₂CH₃

TABLE 2h

No. X₁—X₂—X₃ 2h-1

2h-2

2h-3

2h-4

2h-5

2h-6

TABLE 2i

No. X₁—X₂—X₃ 2i-1

2i-2

2i-3

2i-4

2i-5

2i-6

TABLE 2j

No. X₁—X₂—X₃ 2j-1

2j-2

2j-3

2j-4

2j-5

2j-6

TABLE 2k

No. X₁—X₂—X₃ 2k-1

2k-2

2k-3

2k-4

2k-5

2k-6

TABLE 3a No. R₁ X₁—X₂—X₃

3a-1 3a-2 CH₃ H

3a-3 3a-4 3a-5 3a-6 3a-7 CH₃ H H₃N⁺C(CH₂OH)₃ Na ½Ca

3a-8 H

3a-9 H

3a-10 3a-11 CH₃ H

3a-12 3a-13 CH₃ H

3a-14 CH₃

3a-15 3a-16 CH₃ H

3a-17 3a-18 CH₃ H

3a-19 3a-20 CH₃ H

3a-21 3a-22 CH₃ H

3a-23 3a-24 CH₃ H

3a-25 H —CH₂)₃CH₃ 3a-26 CH₃ —(CH₂)₇CH₃ 3a-27 H 3a-28 CH₃

3a-29 H

3a-30 CH₃

3a-31 3a-32 3a-33 CH₃ H Na

3a-34 3a-35 H Na

TABLE 3b

No. R₁ X₁—X₂—X₃ 3b-1 CH₃

3b-2 H 3b-3 H

3b-4 H

TABLE 3c

No. R₁ X₁—X₂—X₃ 3c-1 H

TABLE 3d No. R₁ X₁—X₂—X₃

3d-1 3d-2 ½Ca Na

3d-3 Na

3d-4 Na

3d-5 3d-6 CH₃ H

3d-7 3d-8 3d-9 CH₃ H Na

3d-10 3d-11 3d-12 3d-13 CH₃ H Na ½Ca

3d-14 3d-15 H Na

3d-16 H

3d-17 H

3d-18 H —(CH₂)₃CH₃ 3d-19 CH₃ —NHCH₃ 3d-20 H 3d-21 3d-22 CH₃ H

3d-23 H

3d-24 H

3d-25 3d-26 H Na

racemic compound 3d-27 3d-28 H Na

racemic compound 3d-29 3d-30 H Na

racemic compound

TABLE 3e

No. R₁ X₁—X₂—X₃ 3e-1 ½Ca

Physicochemical properties of compounds above are shown below. The compound number below corresponds to that described in Tables above.

No. 1a-4

[α]_(D)=−11.5° (CHCl₃, c=1.01, 23.5° C.).

No. 1a-5

[α]_(D)=−10.0° (CHCl₃, c=1.01, 25.0° C.).

No. 1a-6

CDCl₃ 300 MHz

0.93-1.96(14H, m), 2.20-2.26(3H, m), 3.03(1H, m), 3.67(3H, s), 4.99(1H, d, J=6.6 Hz), 5.10-5.24(2H, m), 7.37-7.51(3H, m), 7.54-7.64(3H, m), 7.76-7.88(2H, m), 8.11(1H, m).

IR (CHCl₃): 3384, 3278, 3026, 2952, 2874, 1727, 1436, 1411, 1324, 1155, 1097/cm.

[α]_(D)=−9.0° (CHCl₃, c=1.04, 22.0° C.).

No. 1a -7

CDCl₃ 300 MHz

0.93-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 3.04(1H, m), 5.15-5.25(2H, m), 5.28(1H, d, J=6.9 Hz), 7.36-7.50(3H, m), 7.54-7.63(3H, m), 7.76-7.89(2H, m), 8.12(1H, m).

IR(CHCl₃): 3268, 3028, 2952, 2872, 1708, 1452, 1410, 1324, 1155, 1097/cm.

[α]_(D)=−9.1° (CHCl₃, c=1.01, 24.0° C.).

No. 1a-8

CDCl₃ 300 MHz

0.9-1.99(14H, m), 2.21-2.29(3H, m), 3.05(1H, m), 3.67(3H, s), 4.92(1H, d, J=6.3 Hz), 5.14-5.30(2H, m), 7.70-7.78(6H, m), 7.96-8.01(2H, m).

IR(CHCl₃): 3376, 3272, 3018, 2946, 2868, 1727, 1616, 1435, 1388, 1324, 1162, 1130, 1069/cm.

[α]_(D)=+1.6° (CHCl₃, c=1.01, 24.0° C.). mp. 117-119° C.

No. 1a -9

CDCl₃ 300 MHz

0.95-2.08(14H, m), 2.19(1H, m), 2.32(2H, t, J=7.2 Hz), 3.06(1H, m), 5.20-5.30(2H, m), 5.34(1H, d, J=6.6 Hz), 7.69-7.78(6H, m), 7.96-8.03(2H, m).

IR(CHCl₃): 3260, 3020, 2950, 2868, 1708, 1389, 1324, 1162, 1130, 1069/cm.

[α]_(D)=+13.3° (CHCl₃, c=1.05, 24.0° C.).

mp. 118-120° C.

No. 1a-10

CDCl₃ 300 MHz

0.96-1.98(14H, m), 2.15-2.32(3H, m), 3.04(1H, m), 3.66(3H, s), 5.12-5.26(5H, m), 7.67-7.78(4H, m), 7.93-8.07(4H, m).

IR(CHCl₃): 3276, 3018, 2946, 2868, 1726, 1595, 1435, 1341, 1162, 1095/cm.

[α]_(D)=−1.5° (CHCl₃, c=1.01, 25.0° C.).

mp. 133-139° C.

No. 1a-11

CD₃OD 300 MHz

1.05-1.98(14H, m), 2.13-2.22(3H, m), 2.97(1H, m), 5.09-5.22(2H, m), 7.85-7.92(4H, m), 7.95-8.05(4H, m).

IR(KBr): 3385, 3261, 3069, 3003, 2954, 2872, 1708, 1596, 1428, 1413, 1378, 1343, 1326, 1236, 1186, 1160, 1096/cm.

mp. 144-146° C.

No. 1a-12

CDCl₃ 300 MHz

0.96-1.96(14H, m), 2.22-2.27(3H, m), 3.03(1H, m), 3.66(3H, s), 3.87(3H, s), 4.86(1H, d, J=6.9 Hz), 5.18-5.24(2H, m), 6.99-7.02(2H, m), 7.55-7.66(2H, m), 7.66-7.69(2H, m), 7.89-7.92(2H, m).

IR(CHCl₃): 3374, 3270, 3016, 2948, 2870, 1726, 1608, 1518, 1487, 1458, 1437, 1248, 1157, 1037.

[α]_(D)=+4.2° (CHCl₃, c=1.01, 24° C.).

mp. 85-87° C.

No. 1a-13

CDCl₃ 300 MHz

0.97-1.99(14H, m), 2.18(1H, m), 2.30(2H, t, J=7.2 Hz), 3.04(1H, m), 3.86(3H, s), 5.18(1H, d, J=5.7 Hz), 5.23-5.26(2H, m), 6.99-7.02(2H, m), 7.55-7.58(2H, m), 7.66-7.68(2H, m), 7.89-7.92(2H, m).

IR(CHCl₃): 3380, 3260, 3020, 2948, 2868, 1708, 1608, 1519, 1487, 1458, 1306, 1293, 1248, 1156/cm.

[α]_(D)=+18.3° (CHCl₃, c=1.00, 25.5° C.)

No. 1a-14

CDCl₃ 300 MHz

0.98-2.00(14H, m), 2.20(1H, m), 2.25(2H, t, J=7.2 Hz), 3.02(1H, m), 3.67(3H, s), 4.85(1H, d, J=6.3 Hz), 5.19-5.25(2H, m), 7.13(1H, dd, J=4.8, 3.6 Hz), 7.39(1H, d, J=4.8 Hz), 7.40(1H, d, J=3.6 Hz), 7.71-7.74(2H, m), 7.86-7.89(2H, m).

IR(CHCl₃): 3374, 3270, 3018, 2946, 2868, 1727, 1593, 1434, 1322/cm.

[α]_(D)=+5.6° (CHCl₃, c=1.01, 24° C.).

mp. 69-71° C.

No. 1a-15

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.03(1H, m), 5.20(1H, d, J=6.9 Hz), 5.24-5.28(2H, m), 7.13(1H, dd, J=4.8, 3.3 Hz), 7.38(1H, d, J=4.8 Hz), 7.43(1H, d, J=3.3 Hz), 7.73(2H, d, J=8.4 Hz), 7.87(2H, d, J=8.4 Hz).

IR(CHCl₃): 3260, 3022, 2948, 2868, 1709, 1593, 1404, 1321, 1154/cm.

[α]_(D)=+20.8° (CHCl₃, c=1.07, 23° C.).

mp. 71-73° C.

No. 1a-16

CDCl₃ 300 MHz

0.98-2.00(14H, m), 2.27(2H, t, J=7.5 Hz), 2.28(1H, m), 3.13(1H, m), 3.66(3H, s), 4.90(1H, d, J=6.9 Hz), 5.25-5.29(2H, m), 7.40-7.65(6H, m), 7.76(1H, d, J=8.4 Hz), 7.90-8.02(4H, m).

IR(CHCl₃): 3376, 3276, 3018, 2946, 2868, 1726, 1593, 1435, 1394, 1322, 1159/cm.

[α]_(D)=+7.0° (CHCl₃, c=1.07, 24° C.).

No. 1a-17

CDCl₃ 300 MHz

1.02-2.07(14H, m), 2.25(1H, m), 2.34(2H, t, J=6.6 Hz), 3.14(1H, m), 5.28-5.33(3H, m), 7.39-7.57(4H, m), 7.62-7.65(2H, m), 7.76(1H, d, J=8.1 Hz), 7.89-8.02(4H, m).

IR(CHCl₃): 3260, 2948, 2868, 1709, 1593, 1394, 1324, 1157/cm.

[α]_(D)=+20.2° (CHCl₃, c=1.02, 24° C.).

No. 1a-18

CDCl₃ 300 MHz

1.05-1.97(14H, m), 2.25(2H, t, J=7.2 Hz), 2.33(1H, m), 3.12(1H, m), 3.67(3H, s), 4.91(1H, d, J=6.6 Hz), 5.24-5.29(2H, m), 7.24(1H, d, J=3.9 Hz), 7.39-7.45(3H, m), 7.56(1H, d, J=3.9 Hz), 7.59-7.62(2H, m).

IR(CHCl₃): 3372, 3272, , 3018, 2946, 2868, 1727, 1433, 1331, 1152/cm.

[α]_(D)=−5.7° (CHCl₃, c=1.01, 23° C.).

No. 1a-19

CDCl₃ 300 MHz

1.05-2.05(14H, m), 2.28-2.33(3H, m), 3.13(1H, m), 5.18(1H, d, J=6.3 Hz), 5.27-5.31 (2H, m), 7.24(1H, d, J=4.2 Hz), 7.39-7.42(3H, m), 7.56(1H, d, J=4.2 Hz), 7.58-7.62(2H, m).

IR(CHCl₃): 3372, 3254, 3018, 2948, 2868, 1707, 1431, 1328, 1151/cm.

[α]_(D)=+4.5° (CHCl₃, c=1.01, 21.5° C.).

No. 1a -20

CDCl₃ 300 MHz

1.05-2.00(14H, m), 2.26(2H, t, J=7.5 Hz), 2.33(1H, m), 3.11(1H, m), 3.68(3H, s), 4.92(1H, d, J=6.0 Hz), 5.27(2H, m), 7.05(1H, m), 7.10(1H, d, J=3.6 Hz), 7.25(1H, m), 7.32(1H, m), 7.49(1H, d, J=3.6 Hz).

IR(CHCl₃): 3372, 3272, 3018, 2946, 2686, 1727, 1438, 1417, 1333, 1151/cm.

[α]_(D)=−9.2° (CHCl₃, c=1.01, 25° C.).

No. 1a-21

CDCl₃ 300 MHz

1.02-2.01(14H, m), 2.28-2.34(3H, m), 3.13(1H, m), 5.12(1H, d, J=6.9 Hz), 5.28-5.32(2H, m), 7.06(1H, m), 7.10(1H, d, J=3.9 Hz), 7.25(1H, m), 7.32(1H, m), 7.50(1H, d, J=3.9 Hz).

IR(CHCl₃): 3350, 3250, 2948, 1709, 1440, 1420, 1330, 1151.

[α]_(D)=+2.5° (CHCl₃, c=1.00, 25° C.).

No. 1a-22

CDCl₃ 300 MHz

0.96-2.05(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.0 Hz), 3.11(1H, m), 5.20-5.34(2H, m), 5.41(1H, d, J=6.6 Hz), 7.31-7.49(5H, m), 7.62(1H, d, J=7.8 Hz), 8.11(1H, d.d, J=1.8 and 7.8 Hz), 8.35(1H, d, J=1.8 Hz).

IR(CHCl₃): 3384, 3271, 3025, 2958, 1708, 1608, 1559, 1537, 1357, 1168/cm.

[α]_(D)=+18.3° (CHCl₃, c=0.31, 22° C.).

No. 1a-23

CDCl₃ 300 MHz

0.97-2.07(14H, m), 2.24(1H, m), 2.35(2H, t, J=6.9 Hz), 3.09(1H, m), 3.86(3H, s), 5.24-5.35(2H, m), 5.44(1H, d, J=6.3 Hz), 6.97-7.00(2H, m), 7.26-7.28(2H, m), 7.59(1H, d, J=8.1 Hz), 8.06(1H, d.d, J=2.1 and 8.1 Hz), 8.29(1H, d, J=2.1 Hz).

IR(CHCl3): 3384, 3270, 2959, 1709, 1609, 1535, 1519, 1357, 1302, 1255, 1226, 1169/cm.

[α]_(D)=+17.0° (CHCl₃, c=1.00, 21° C.).

No. 1a-24

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.20-2.25(1H, m), 2.26(2H, t, J=7.2 Hz), 3.02-3.10(1H, m)

3.66(3H, s), 4.92(1H, d, J=6.6 Hz), 5.16-5.31(2H, m), 7.52-7.60(3H, m), 7.94-8.06(6H, m).

IR(CHCl₃): 3376, 3020, 2946, 2868, 1726, 1436, 1366, 1298, 1164, 1090, 890/cm.

[α]_(D)=+11.2±0.5° (CHCl₃, c=1.04, 23.5° C.)

mp. 101-103° C.

No. 1a-25

CDCl₃ 300 MHz

0.95-2.08(14H, m), 2.15-2.22(1H, m), 2.33(2H, t, J=6.9 Hz), 3.02-3.10(1H, m), 5.21-5.31(2H, m), 5.34(1H, d, J=6.3 Hz), 7.51-7.59(3H, m), 7.92-8.07(6H, m).

IR(CHCl₃): 3258, 3022, 2948, 2868, 1707, 1399, 1328, 1298, 1163, 1089, 1051, 892/cm.

[α]_(D)=+29.8±0.7° (CHCl₃, c=1.05, 25° C.)

mp. 158-160° C.

No. 1a -26

Anal. Calcd for C₂₆H₃₀N₃O₄SNa 0.8H₂O: C, 60.29; H, 6.15; N, 8.11; S, 6.19; Na, 4.44; Found: C, 60.15; H, 6.19; N, 8.15; S, 6.03; Na, 4.98.

[α]_(D)=−16.6° (CHCl₃, c=1.04, 25.0° C.).

No. 1a-27

CDCl₃ 300 MHz

0.92-1.98(14H, m), 2.20(1H, m), 2.26(2H, t, J=7.5 Hz), 3.03(1H, m), 3.12(6H, s), 3.66(3H, s), 4.87(1H, d, J=6.6 Hz), 5.16 -5.3 2(2H, m), 6.73-6.80(2H, m) 7.88-8.00(6H, m).

IR(CHCl₃): 3376, 3020, 2946, 1726, 1601, 1518, 1442, 1419, 1362, 1312, 1163, 1133, 1088/cm.

[α]_(D)=+55.3° (CHCl₃, c=0.53, 24.0° C.).

mp. 158-168° C.

No. 1a-28

CDCl₃+CD₃OD 300 MHz

0.99-2.14(14H, m), 2.21(1H, m), 2.31(2H, t, J=7.2 Hz), 2.94(1H, m), 3.12(6H, s), 5.22-5.38(2H, m), 6.73-6.81(2H, m), 7.87-8.00(6H, m).

IR(KBr): 3434, 3309, 2946, 1708, 1604, 1520, 1442, 1416, 1366, 1312, 1252, 1164, 1155, 1134, 1091/cm.

[α]_(D)=not measurable (colored, insufficient energy)

mp. 193-196° C.

No. 1a-29

CD₃OD 300 MHz

1.02-1.96(14H, m), 2.10(2H, t, J=7.8 Hz), 2.16(1H, m), 2.98(1H, m), 3.11(6H,s), 5.07-5.27(2H, m), 6.80-6.87(2H, m), 7.84-8.00(6H, m).

IR(KBr): 3433, 3087, 3004, 2949, 2871, 1604, 1565, 1520, 1444, 1420, 1364, 1312, 1253, 11638, 1136, 1090/cm.

[α]_(D)=not measurable

No. 1a-30

CDCl₃ 300 MHz

0.95-1.99(14H, m), 2.22(1H, m), 2.26(2H, t, J=7.2 Hz), 2.35(3H, s), 3.06(1H, m) 3.66(3H, s), 4.95(1H, d, J=6.9 Hz), 5.15-5.30(2H, m), 7.26-7.32(2H, m), 7.97-8.06(6H, m).

IR(CHCl₃): 3374, 2996, 2946, 2868, 1763, 1728, 1591, 1495, 1435, 1368, 1299, 1228, 1192, 1163, 1139/cm.

[α]_(D)=+12.9° (CHCl₃, c=1.04, 26.0° C.).

No. 1a-31

CDCl₃ 300 MHz

0.93-2.01(14H, m), 2.19(1H, m), 2.31(2H, t, J=7.2 Hz), 2.35(3H, s), 3.06(1H, m), 5.17-5.32(2H, m), 7.25-7.32(2H, m), 7.96-8.07(6H, m).

IR(CHCl₃): 3267, 3028, 2952, 2874, 1759, 1708, 1592, 1495, 1368, 1328, 1299, 1163, 1138, 1088, 1050, 1008/cm.

[α]_(D)=+21.7° (CHCl₃, c=0.51, 22° C.).

No. 1a-32

CDCl₃ 300 MHz

0.93-1.99(14H, m), 2.21(1H, m), 2.27(2H, t, J=7.2 Hz), 3.05(1H, m), 3.67(3H, s), 4.92(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 6.72(1H, s), 6.96-7.00(2H, m), 7.86-8.04(6H, m).

IR(CHCl₃): 3374, 3276, 3018, 2946, 2686, 1725, 1605, 1589, 1502, 1433, 1396, 1330, 1271, 1164, 1135, 1089/cm.

[α]_(D)=+18.6° (CHCl₃, c=1.00, 26.0° C.).

No. 1a-33

CDCl₃+CD₃OD 300 MHz

0.98-2.08(14H, m), 2.20(1H, m), 2.28(2H, t, J=7.2 Hz), 2.98(1H, m), 5.18-5.32(2H, m), 6.92-6.99(2H, m), 7.85-8.02(6H, m).

IR(KBr): 3385, 3248, 2948, 2876, 1717, 1601, 1505, 1430, 1399, 1296, 1280, 1219, 1165, 1136, 1092/cm.

[α]_(D)=−16.0° (CH₃OH, c=1.08, 26.0° C.).

mp. 208-210° C.

No. 1a-34

mp. 82-83° C.

[α]_(D)=+10.6° (CHCl₃, c=1.01, 23.5° C.).

No. 1a -35

mp. 80-82° C.

[α]_(D)=−1.8° (CHCl₃, c=1.07, 22.0° C.).

No. 1a-36

TLC Rf=0.25 (ethyl acetatein-hexane=1:1 (0.3% acetic acid))

No. 1a-37

CDCl₃ 300 MHz

0.92-1.96(14H, m), 2.21(1H, m), 2.27(2H, t, J=7.4 Hz), 3.01(1H, m), 3.66(3H, s), 4.71(1H, d, J=6.6 Hz), 5.14-5.29(2H, m), 7.12(1H, d, J=16.2 Hz), 7.24(1H, d, J=16.2 Hz), 7.28-7.42(3H, m), 7.52-7.56(2H, m), 7.62(2H, d, J=8.7 Hz), 7.85(2H, d, J=8.7 Hz).

IR(CHCl₃): 3384, 3283, 3023, 2954, 2876, 1730, 1595, 1494, 1317, 1163, 1147/cm.

[α]_(D)=+10.5° (CHCl₃, c=1.01, 24° C.).

mp 116-117° C.

No. 1a-38

CDCl₃ 300 MHz

0.92-1.99(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.02(1H, m), 5.23-5.29(3H, m), 7.11(1H, d, J=16.2 Hz), 7.23(1H, d, J=16.2 Hz), 7.28-7.4 1(3H, m), 7.52-7.55(2H, m), 7.61(2H, d, J=8.7 Hz), 7.86(2H, d, J=8.7 Hz).

IR(CHCl₃): 3515, 3384, 3270, 3022, 3015, 2957, 2876, 2669, 1708, 1595, 1496, 1320, 1157/cm.

[α]_(D)=+27.1° (CHCl₃, c=1.02, 24° C.).

No. 1a-39

CDCl₃ 300 MHz

0.92-1.99(14H, m), 2.15(1H, m), 2.28(2H, t, J=7.4 Hz), 3.01(1H, m), 3.68(3H, s), 4.96(1H, d, J=6.6 Hz), 5.16-5.32(2H, m), 6.60(1H, d, J=12.0 Hz), 6.74(1H, d, J=12.0 Hz), 7.16-7.23(5H, m), 7.35(2H, d, J=8.4 Hz), 7.72(2H, d, J=8.4 Hz).

IR(CHCl₃): 3384, 3283, 3023, 3015, 2954, 2876, 1730, 1595, 1493, 1324, 1163, 1147/cm.

[α]_(D)=+13.7° (CHCl₃, c=1.00, 24° C.).

No. 1a-40

CDCl₃ 300 MHz

0.90-2.16(14H, m), 2.12(1H, m), 2.34(2H, t, J=7.2 Hz), 3.02(1H, m), 5.16(1H, d, J=6.9 Hz), 5.23-5.34(2H, m), 6.60(1H, d, J=12.3 Hz), 6.74(1H, d, J=12.3 Hz), 7.14-7.24(5H, m), 7.35(2H, d, J=8.1 Hz), 7.72(2H, d, J=8.1 Hz).

IR(CHCl₃): 3515, 3384, 3269, 3025, 3021, 3014, 2957, 2876, 2668, 1709, 1595, 1322, 1162, 1147/cm.

[α]_(D)=+26.40° (CHCl₃, c=1.00, 24° C.).

No. 1a-41

CDCl₃ 300 MHz 0.98-1.99(14H, m), 2.17(1H, m), 2.32(2H, t, J=7.2 Hz), 3.00(1H, m), 3.84(3H, s, 5.20-5.26(3H, m), 6.90-6.95(2H, m), 6.98(1H, d, J=16.2 Hz), 7.17(1H, d, J=16.2 Hz), 7.46-7.49(2H, m), 7.58(2H, d, J=8.4 Hz), 7.83(2H, d, J=8.4 Hz).

IR(CHCl₃): 3258, 3018, 3002, 2950, 1709, 1590, 1509, 1457, 1404, 1302, 1250, 1153/cm.

[α]_(D)=+30.2° (CHCl₃, c=1.00, 23° C.).

mp. 99-100° C.

No. 1a-42

CDCl₃ 300 MHz 1.01-1.99(14H, m), 2.28(2H, t, J=7.2 Hz), 2.30(1H, m), 3.10(1H, m), 3.66(3H, s), 5.07(1H, br), 5.25-5.30(2H, m), 6.98-7.04(2H, m), 7.16(1H, d, J=16.2 Hz), 7.28-7.37(3H, m), 7.47-7.50(3H, m).

IR(CHCl₃): 3372, 3276, 3020, 2946, 2870, 1727, 1491, 1433, 1331, 1152/cm.

[α]_(D)=−11.5° (CHCl₃, c=1.07, 21.5° C.).

No. 1a-43

CDCl₃ 300 MHz

0.98-2.00(14H, m), 2.11-2.36(3H, m), 3.12(1H, m), 5.10(1H, d, J=6.6 Hz), 5.29-5.32(2H, m), 6.99-7.04(2H, m), 7.23(1H, d, J=21.6 Hz), 7.32-7.49(6H, m).

[α]_(D)=+3.4° (CHCl₃, c=1.03, 25° C.).

IR(CHCl₃): 3380, 3248, 3020, 2948, 2868, 1709, 1491, 1430, 1329, 1151/cm.

No. 1a-44

CDCl₃ 300 MHz

1.00-2.00(14H, m), 2.13(1H, m), 2.29(2H, t, J=7.4 Hz), 2.90-3.13(5H, m), 3.68(3H, s), 4.74(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 7.18-7.29(7H, m), 7.76(2H, d, J=8.1 Hz).

IR(CHCl₃): 3384, 3282, 3063, 3028, 3023, 3016, 2953, 2876, 1730, 1599, 1496, 1319, 1157/cm.

[α]_(D)=+2.3° (CHCl₃, c=1.00, 25° C.).

mp. 85.0-86.0° C.

No. 1a-45

CDCl₃ 300 MHz

0.90-2.05(14H, m), 2.09(1H, m), 2.35(2H, t, J=6.9 Hz), 2.90-3.13(5H, m), 5.18(1H, d, J=6.6 Hz), 5.24-5.34(2H, m), 7.10-7.27(7H, m), 7.76(2H, d, J=8.4 Hz).

IR(CHCl₃): 3510, 3384, 3270, 3087, 3063, 3026, 3018, 3014, 2955, 2876, 2670, 1708, 1599, 1496, 1318, 1157/cm.

[α]_(D)=+8.50° (CHCl₃, c=1.01, 25° C.).

No. 1a-46

[α]_(D)=+6.80° (CHCl₃, c=1.05, 25° C.).

mp. 99-100° C.

No. 1a-47

CDCl₃ 300 MHz

0.97-2.01(14H, m), 2.14(1H, m), 2.36(2H, t, J=7.2 Hz), 3.02(1H, m), 5.23(1H, d, J=5.4 Hz), 5.26-5.30(2H, m), 7.37-7.39(3H, m), 7.54-7.58(2H, m), 7.63-7.66(2H, m), 7.85-7.88(2H, m).

IR(CHCl₃): 3375, 3260, 3022, 2948, 2212, 1707, 1596, 1497, 1396, 1322, 1160/cm.

[α]_(D)=+25.0° (CHCl₃, c=1.02, 24° C.).

mp. 117-118° C.

No. 1a-48

CD₃OD 300 MHz

1.05-1.93(14H, m), 2.10-2.15(3H, m), 2.96(1H, m), 5.08-5.28(2H, m), 7.38-7.40(3H, m), 7.554-7.56(2H, m), 7.69(1H, d, J=8.4 Hz), 7.87(1H, d, J=8.4 Hz).

No. 1a-49

CDCl₃ 300 MHz

0.96-1.97(14H, m), 2.24(1H ,m), 2.31(2H, t, J=6.9 Hz), 3.05(1H, m), 3.69(3H, s), 5.15(1H, d, J=6.6 Hz), 5.25-5.27(2H, m), 7.40-7.43(3H, m), 7.61-7.64(2H, m), 7.85(1H, d, J=8.1 Hz), 8.07(1H, dd, J=8.1, 1.8 Hz), 8.58(1H, d, J=1.8 Hz).

IR(CHCl₃): 3374, 3020, 2948, 2870, 2212, 1726, 1606, 1530, 1493, 1437, 1345, 1167/cm.

[α]_(D)=+2.4° (CHCl₃, c=1.03, 25° C.).

mp. 77-79° C.

No. 1a -50

CDCl₃ 300 MHz

1.00-2.02(14H, m), 2.20(1H, m), 2.34(2H, t, J=6.6 Hz), 3.08(1H, m), 5.26-5.29(2H, m), 5.41(1H, d, J=6.9 Hz), 7.40-7.43(3H, m), 7.61-7.64(2H, m), 7.84(1H, d, J=8.1 Hz), 8.07(1H, dd, J=8.4, 1.8 Hz), 8.57(1H, dd, J=1.8 Hz).

IR(CHCl₃): 3380, 3254, 2952, 2880, 2212, 1707, 1606, 1531, 1493, 1409, 1344, 1166.

[α]_(D)=+23.4° (CHCl₃, c=1.00, 25° C.).

No. 1a-51

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.23(1H, m), 2.30(2H, t, J=7.2 Hz), 3.00(1H, m), 3.66(3H, s), 4.56(2H, br), 4.70(1H, d, J=6.9 Hz), 5.20-5.29(2H, m), 7.15(1H, dd, J=7.8, 1.8 Hz), 7.23(1H, d, J=1.8 Hz), 7.36-7.39(3H, m), 7.46(1H, d, J=7.8 Hz), 7.53-7.56(2H, m).

IR(CHCl₃): 3494, 3386, 3028, 2952, 2874, 1725, 1611, 1559, 1497, 1422, 1317, 1162/cm.

No. 1a-52

CDCl₃ 300 MHz

0.96-2.04(16H, m), 2.20(1H, m), 2.36(2H, t, J=6.9 Hz), 2.99(1H, m), 5.17(1H, d, J=6.3 Hz), 5.28-5.31(2H, m), 7.18(1H, dd, J=9.6, 1.8 Hz), 7.25(1H, m), 7.36-7.39(3H, m), 7.46(1H, d, J=7.8 Hz), 7.52-7.56(2H, m).

IR(CHCl₃): 3482, 3378, 3260, 3022, 2948, 2868, 1708, 1612, 1495, 1422, 1317/cm.

[α]_(D)=+15.0° (CHCl₃, c=1.00, 24° C.).

No. 1a-53

CDCl₃ 300 MHz

1.01-2.05(15H, m), 2.3 1(2H, t, J=7.2 Hz), 3.10(1H, m), 3.67(3H, s), 5.02(1H, br), 5.26-5.33(2H, m), 7.18(1H, d, J=4.2 Hz), 7.36-7.39(3H, m), 7.48(1H, d, J=4.2 Hz), 7.51-7.55(2H, m).

IR(CHCl₃): 3372, 3270, 3018, 3004, 2946, 2868, 2202, 1726, 1486, 1433, 1336, 1154/cm.

[α]_(D)=+0.60° (CHCl₃, c=1.11, 25° C.), [α]₄₃₆+17.8° (CHCl₃, c=1.11, 25° C.)

No. 1a-54

CDCl₃ 300 MHz

0.99-2.11(14H, m), 2.27(1H, m), 2.37(2H, t, J=7.5 Hz), 3.13(1H, m), 5.16(1H, d, J=6.6 Hz), 5.31-5.35(2H, m), 7.18(1H, d, J=3.6 Hz), 7.37-7.39(3H, m), 7.50(1H, d, J=3.6 Hz), 7.52-7.55(2H, m).

IR(CHCl₃): 3484, 3370, 3246, 2948, 2868, 2202, 1708, 1486, 1429, 1335, 1153/cm.

[α]_(D)=+17.8° (CHCl₃, c=1.00, 24C.). mp. 95-96° C.

No. 1a-55

CDCl₃ 300 MHz

0.95-1.92(14H, m), 2.15(1H, m), 2.24(2H, t, J=7.5 Hz), 3.00(1H, m), 3.66(3H, s), 5.10-5.30(3H, m), 7.40-7.60(7H, m), 7.70(1H, d, J=7.8 Hz), 8.08(1H, d, J=8.1 Hz).

IR(CHCl₃): 3356, 3020, 2948, 2868, 2210, 1727, 1490, 1458, 1437, 1341, 1165/cm.

[α]_(D)=−58.4° (CHCl₃, c=1.00, 26° C.).

mp. 84-85° C.

No. 1a-56

CDCl₃ 300 MHz

0.95-1.95(14H, m), 2.10(1H, m), 2.27(2H, t, J=6.9 Hz), 3.00(1H, m), 5.17-5.21(2H, m), 5.38(1H, d, J=6.9 Hz), 7.39-7.60(7H, m), 7.70(1H, dd, J=7.8, 1.5 Hz), 8.07(1H, J=6.6, 1.5 Hz).

IR(CHCl₃): 3364, 3026, 2952, 2874, 2212, 1707, 1597, 1491, 1458, 1411, 1341, 1164/cm.

[α]_(D)=−43.1° (CHCl₃, c=1.00, 25° C.).

No. 1a-57

CDCl₃ 300 MHz

0.99-1.97(14H, m), 2.23-2.30(3H, m), 3.01(1H, m), 3.67(3H, s), 5.17-5.26(3H, m), 7.36-7.38(3H, m), 7.50-7.56 (3H, m), 7.60( 1H, m), 7.83 (1H, m), 8.05(1H, m).

IR(CHCl₃): 3376, 3020, 2946, 2870, 1727, 1598, 1491, 1437, 1412, 1330, 1245, 1163/cm.

[α]_(D)=−12.7° (CHCl₃, c=1.00, 24° C.).

No. 1a-58

CDCl₃ 300 MHz

0.97-1.98(14H, m), 2.20(1H, m), 2.33(2H, t, J=6.9 Hz), 3.02(1H, m), 5.19-5.28(3H, m), 7.36-7.38(3H, m), 7.47-7.55(3H, m), 7.69(1H, m), 7.83(1H, m), 8.04(1H, m).

IR(CHCl₃): 3376, 3260, 3022, 3002, 2948, 2868, 2220, 1708, 1598, 1490, 1455, 1412, 1327, 1162/cm.

[α]_(D)=8.6° (CHCl₃, c=1.01, 24° C.).

No. 1a-59

CDCl₃ 300 MHz

0.95-1.99(24H, m), 2.20(1H, m), 2.28(2H, t, J=7.8 Hz), 2.53(1H, s), 2.96(1H, m), 3.69(3H, s), 4.99(1H, d, J=6.6 Hz), 5.18-5.20(2H, m), 7.53(2H, d, J=8.4 Hz), 7.82(2H, d, J=8.4 Hz).

IR(CHCl₃): 3583, 3376, 3002, 2936, 2852, 1725, 1591, 1490, 1437, 1393, 1325, 1160/cm.

[α]_(D)=−8.8° (CHCl₃, c=1.00, 24° C.).

No. 1 a-60

CDCl₃ 300 MHz

0.96-2.05(24H, m), 2.22(1H, m), 2.33(2H, m), 2.88(1H, m), 5.22-5.26(2H, m), 5.30(1H, d, J=5.7 Hz), 7.50(2H, d, J=8.7 Hz), 7.80(2H, d, J=8.7 Hz).

IR(CHCl₃): 3376, 3260, 3022, 2936, 2852, 1710, 1592, 1491, 1452, 1395, 1325, 1159/cm.

[α]_(D)=−8.9° (CHCl₃, c=1.06, 24° C.),

mp. 88-91° C.

No. 1a-61

CDCl₃ 300 MHz

0.95-2.24(23H, m), 2.29(2H, m), 2.99(1H, m), 3.69(3H, s), 4.76(1H, d, J=6.3 Hz), 5.21-5.24(2H, m), 6.28(1H, m), 7.50-7.53(2H, m), 7.77-7.80(2H, m).

IR(CHCl₃): 3374, 3270, 3018, 2942, 2868, 2196, 1726, 1589, 1490, 1435, 1324, 1158/cm.

[α]_(D)=+7.7° (CHCl₃, c=1.02, 24° C.),

mp. 93-95° C.

No. 1a-62

CDCl₃ 300 MHz

0.96-2.45(23H, m), 2.36(2H, d, J=6.9 Hz), 2.99(1H, m), 5.24(1H, d, J=6.3 Hz), 5.24-5.32(2H, m), 6.28(1H, m), 7.50-7.53(2H, m), 7.78-7.81(2H, m).

IR(CHCl₃):3468, 3374, 3260, 3020, 2942, 2868, 2196, 1598, 1490, 1455, 1398, 1322, 1157/cm.

[α]_(D)=+19.4° (CHCl₃, c=1.03, 24° C.).

No. 1a-63

CDCl₃ 300 MHz

0.93-1.95(25H, m), 2.16(1H, m), 2.29(2H, t, J=7.2 Hz), 2.43(2H, t, J=6.9 Hz), 2.94(1H, m), 3.69(3H, s), 4.95(1H, d, J=6.9 Hz), 5.21-5.24(2H, m), 7.49(2H, d, J=8.7 Hz), 7.79(2H, J=8.7 Hz).

IR(CHCl₃): 3376, 3018, 2946, 2866, 2222, 1727, 1592, 1456, 1435, 1325, 1158/cm.

[α]_(D)=+3.7° (CHCl₃, c=1.00, 25° C.).

No. 1a-64

CDCl₃ 300 MHz

0.93-1.97(26H, m), 2.35(2H, t, J=7.2 Hz), 2.43(2H, t, J=7.2 Hz), 3.00(1H, m), 5.08(1H, d, J=6.6 Hz), 5.26-5.27(2H, m), 7.49(2H, d, J=8.7 Hz), 7.78(2H, d, J=8.7 Hz).

IR(CHCl₃): 3260, 3020, 2948, 2864, 2222, 1708, 1592, 1489, 1456, 1397, 1324, 1156/cm.

[α]_(D)=+14.4° (CHCl₃, c=1.00, 25° C.)

mp. 70-71° C.

No. 1a-65

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.18(1H, m), 2.30(2H, t, J=7.2 Hz), 3.00(1H, m), 3.67(3H, s), 4.83(1H, d, J=6.9 Hz), 5.22-5.25(2H, m), 5.54(1H, br), 6.82-6.85(2H, m), 7.42-7.45(2H, m), 7.59-7.62(2H, m), 7.82-7.85(2H, m).

IR(CHCl₃): 3576, 3374, 3018, 2946, 2868, 2208, 1725, 1607, 1587, 1514, 1435, 1325, 1270, 1162, 1133/cm.

[α]_(D)=+9.1° (CHCl₃, c=1.03, 24° C.),

mp. 111-112° C.

No. 1a-66

CDCl₃ 300 MHz

0.97-2.03(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.5 Hz), 3.00(1H, m), 5.17(1H, d, J=6.6 Hz), 5.26-5.30(2H, m), 6.82-6.85(2H, m), 7.42-7.45(2H, m), 7.59-7.62(2H, m, 7.82-7.85(2H, m).

IR(CHCl₃): 3260, 2948, 2870, 2208, 1709, 1607, 1587, 1514, 1396, 1325, 1270, 1162, 1133/cm.

[α]_(D)=−21.0° (CHCl₃, c=1.00, 23° C.),

mp. 161-162° C.

No. 1a-67

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.01(1H, m), 3.67(3H, s), 4.82(1H, d, J=6.6 Hz), 5.19-5.27(2H, m), 7.05-7.10(2H, m), 7.51-7.56(2H, m), 7.61-7.64(2H, m), 7.84-7.87(2H, m).

IR(CHCl₃): 3374, 3280, 3020, 2946, 2868, 2214, 1727, 1589, 1509, 1435, 1327, 1233, 1161, 1134/cm.

[α]_(D)=+6.70° (CHCl₃, c=1.01, 24° C.),

mp. 84-85° C.

No. 1a-68

CDCl₃ 300 MHz

0.96-2.01(14H, m), 2.15(1H, m), 2.34(2H, t, J=6.9 Hz), 3.02(1H, m), 5.23-5.27(3H, m), 7.04-7.10(2H, m), 7.51-7.56(2H, m), 7.61-7.64(2H, m), 7.85-7.88(2H, m).

IR(CHCl₃): 3374, 3258, 3020, 2948, 2868, 2214, 1708, 1589, 1509, 1455, 1398, 1322, 1156/cm.

[α]_(D)=+22.6° (CHCl₃, c=1.02, 24° C.),

mp. 135-136° C.

No. 1a-69

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 2.39(3H, s), 3.01(1H, m), 3.69(3H, s), 4.80(1H, d, J=6.6 Hz), 5.20-5.29(2H, m), 7.18(2H, d, J=8.1 Hz), 7.44(2H, d, J=8.1 Hz), 7.62(2H, d, J=8.4 Hz), 7.84(2H, d, J=8.4 Hz).

IR(CHCl₃): 3374, 3022, 2946, 2868, 2210, 1727, 1589, 1511, 1436, 1323, 1161, 1133/cm.

[α]_(D)=9.2° (CHCl₃, c=1.02, 24° C.).

mp. 116-118° C.

No. 1a-70

CDCl₃ 300 MHz

1.15-2.00(14H, m), 2.13(1H, m), 2.33-2.38(5H, m), 3.04(1H, m), 5.14(1H, d, J=6.6 Hz), 5.25-5.30(2H, m), 7.17(2H, d, J=7.8 Hz), 7.44(2H, d, J=7.8 Hz), 7.62(2H, d, J=8.4 Hz), 7.85(2H, d, J=8.4 Hz).

IR(CHCl₃): 3380, 3260, 3020, 2948, 2868, 2210, 1708, 1590, 1511, 1396, 1324, 1160, 1133/cm.

[α]_(D)=+24.6° (CHCl₃, c=1.00, 24° C.).

No. 1a-71

CDCl₃ 300 MHz

0.95-1.96(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 3.00(1H, m), 3.20(1H, s), 3.65(3H, s), 4.81(1H, d, J=6.6 Hz), 5.20-5.27(2H, m), 7.46-7.54(4H, m), 7.62-7.65(2H, m), 7.85-7.88(2H, m).

IR(CHCl₃): 3374, 3290, 3018, 3002, 2946, 2868, 2212, 2110, 1726, 1591, 1507, 1435, 1401, 1324, 1161/cm.

[α]_(D)=+9.6° (CHCl₃, c=1.01, 24° C.),

mp. 136-138° C.,

No. 1a-72

CDCl₃ 300 MHz

0.96-2.01(14H, m), 2.14(1H, m), 2.35(2H, t, J=7.2 Hz), 3.05(1H, m), 3.20(1H, s), 5.16(1H, d, J=7.2 Hz), 5.26-5.29(2H, m), 7.45-7.53(4H, m), 7.63(2H, d, J=8.4 Hz), 7.87(2H, d, J=8.4 Hz).

IR(CHCl₃): 3462, 3374, 3290, 3024, 2948, 2868, 2212, 2110, 1708, 1591, 1508, 1455, 1401, 1321, 1274, 1160, 1132/cm.

[α]_(D)=+24.30° (CHCl₃, c=1.03, 24° C.),

mp. 96-99° C.

No. 1a-73

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.19(1H, m), 2.27-2.32(5H, m), 3.01(1H, m), 3.67(3H, s), 4.80(1H, d, J=6.6 Hz), 5.20-5.27(2H, m), 7.12(2H, m), 7.56(2H, m), 7.63(2H, m), 7.84(2H, m).

IR(CHCl₃): 3374, 3276, 3018, 2946, 2868, 2214, 1762, 1730, 1589, 1506, 1435, 1368, 1161/cm.

[α]_(D)=+7.8° (CHCl₃, c=1.02, 24° C.),

mp. 102-104° C.

No. 1a-74

CDCl₃ 300 MHz

0.95-2.05(14H, m), 2.15(1H, m), 2.32-2.37(5H, m), 3.02(1H, m), 5.14(1H, d, J=6.6 Hz), 5.26-5.30(2H, m), 7.10-7.13(2H, m), 7.54-7.57(2H, m), 7.62-7.64(2H, m), 7.84-7.87(2H, m).

IR(CHCl₃): 3482, 3250, 3022, 2946, 2868, 2214, 1716, 1709, 1589, 1507, 1454, 1396, 1368, 1322, 1195, 1161/cm.

[α]_(D)=+15.0° (CHCl₃, c=1.00, 24° C.),

mp. 129-131° C.

No. 1a-75

CDCl₃ 300 MHz

0.95-1.99(14H, m), 2.20(2H, m), 2.30(2H, t, J=7.2 Hz), 3.02(1H, m), 3.67(3H, s), 3.94(3H, s), 4.79(1H, d, J=6.6 Hz), 5.19-5.29(2H, m), 7.60-7.63(2H, m), 7.65-7.67(2H, m), 7.86-7.89(2H, m), 8.04-8.06(2H, m).

IR(CHCl3): 3378, 3018, 2946, 2880, 1720, 1604, 1435, 1307, 1276, 1161, 1106/cm.

[α]_(D)=+7.3° (CHCl₃, c=1.01, 25° C.),

mp. 132-133° C.

No. 1a-76

CDCl₃+CD₃OD 300 MHz

1.04-2.05(14H, m), 2.19(1H, m), 2.32(2H, t, J=6.9 Hz), 2.93(1H, m), 5.27-5.31(2H, m), 7.60-7.63(2H, m), 7.65-7.68(2H, m), 7.86-7.89(2H, m), 8.05-8.07(2H, m).

IR(CHCl₃): 3402, 3299, 2955, 2876, 2665, 2549, 1455, 1422, 1313, 1281, 1164/cm.

[α]_(D)=−21.1° (CH₃OH, c=1.03, 23° C.),

mp. 227-229 (dec.)

No. 1a-77

CDCl₃ 300 MHz

0.96-1.99(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.2 Hz), 3.02(1H, m), 3.68(3H, s), 4.88(1H, d, J=6.3 Hz), 5.19-5.29(2H, m), 7.67-7.72(4H, m), 7.89-7.91(2H, m), 8.24-8.27(2H, m).

IR(CHCl₃): 3376, 3276, 3020, 2946, 2870, 2214, 1726, 1594, 1519, 1455, 1435, 1389, 1344, 1161/cm.

[α]_(D)=+7.7° (CHCl₃, c=1.02),

mp. 87-89° C.

No. 1a-78

CDCl₃ 300 MHz

0.98-2.00(14H, m), 2.18(1H, m), 2.34(2H, t, J=7.2 Hz), 3.02(1H, m), 5.24-5.28(2H, m), 5.32(1H, d, J=5.7 Hz), 7.67-7.72(4H, m), 7.89-7.92(2H, m), 8.23-8.26(2H, m).

IR(CHCl₃): 3374, 3260, 2948, 2214, 1708, 1595, 1344, 1160/cm.

[α]_(D)=+23.3° (CHCl₃, c=1.00),

mp. 102-103° C.

No. 1a-79

CDCl₃ 300 MHz

0.93-2.02(14H, m), 2.13(1H, m), 2.36(2H, t, J=7.1 Hz), 3.05(1H, m), 3.84(3H, s), 5.18(1H, br), 5.27-5.31(2H, m), 6.88-6.91(2H, m), 7.48-7.50(2H, m), 7.60-7.63(2H, m), 7.83-7.85(2H, m).

IR(CHCl₃): 3380, 3252, 3020, 2950, 2868, 2208, 1708, 1589, 1511, 1457, 1396, 1321, 1286, 1160/cm.

[α]_(D)=+26.7° (CHCl₃, c=1.00).

mp. 75-77° C.

No. 1a-80

CDCl₃ 300 MHz

0.96 -1.99(14H, m), 2.21(1H, m), 2.30(2H, t, J=7.8 Hz), 3.02(1H, m), 3.68(3H, s) 4.80(1H, d, J=6.6 Hz), 5.19 -5.28(2H, m), 7.51-7.77(5H, m), 7.87-7.90(2H, m), 8.13(1H, m).

IR(CHCl₃): 3374, 3270, 3018, 2946, 2868, 2216, 1726, 1607, 1567, 1527, 1495, 1456, 1436, 1344, 1296, 1161/cm.

[α]_(D)=+7.4° (CHCl₃, c=1.00, 22° C.),

mp. 68-70° C.

No. 1a-81

CDCl₃ 300 MHz

0.97-2.01(14H, m), 2.16(1H, m), 2.34(2H, t, J=7.2 Hz), 3.01(1H, m), 5.22-5.28(3H, m), 7.51(1H, m), 7.65(1H, m) 7.70-7.76(3H, m), 7.88-7.91(2H, m), 8.12(1H, dd, J=6.9 Hz, 1.5 Hz).

IR(CHCl₃): 3480, 3382, 3262, 3026, 2952, 2872, 2218, 1708, 1607, 1567, 1526, 1396, 1343, 1225, 1160/cm.

[α]_(D)=+22.0° (CHCl₃, c=1.00),

mp. 92-94° C.

No. 1a-82

CDCl₃ 300 MHz

0.95-1.98(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.01(1H, m), 3.67(3H, s), 4.30(2H, br), 4.79(1H, d, J=6.9 Hz), 5.20-5.29(2H, m), 6.71-6.76(2H, m), 7.18(1H, m), 7.37(1H, dd, J=7.8, 1.2 Hz), 7.61-7.65(2H, m), 7.83-7.87(2H, m).

IR(CHCl₃): 3376, 3020, 2946, 2868, 2202, 1725, 1613, 1589, 1484, 1454, 1315, 1253, 1161/cm.

[α]_(D)=+8.9° (CHCl₃, c=1.00, 22° C.).

mp. 68-70° C.

No. 1a-83

CDCl₃ 300 MHz

0.97-1.99(14H, m), 2.17(1H, m), 2.33(2H, t, J=6.9 Hz), 2.99(1H, m), 5.20-5.28(2H, m), 5.37(1H, d, J=6.9 Hz), 6.45(2H, br), 6.71-6.76(2H, m), 7.19(1H, dd, J=7.8,6.6 Hz), 7.37(1H, m), 7.62(2H, d, J=8.4 Hz), 7.85(2H, d, J=8.4 Hz).

IR(CHCl₃): 3478, 3378, 3260, 3022, 2950, 2868, 2204, 1708, 1613, 1589, 1484, 1454, 1396, 1316, 1160/cm.

[α]_(D)=+17.1° (CHCl₃, c=1.01).

No. 1a-84

CDCl₃ 300 MHz

1.00-2.08(14H, m), 2.21(1H, m), 2.37(2H, t, J=6.9 Hz), 3.06(1H, m), 3.86(3H, s), 5.29-5.33(2H, m), 5.45(1H, d, J=6.6 Hz), 6.91-6.94(2H, m), 7.56-7.59(2H, m), 7.81(1H, d, t, J=8.1 Hz), 8.04(1H, d.d, J=8.1&1.8 Hz), 8.57(1H, d, J=2.1 Hz).

IR(CHCl₃): 3492, 3254, 3028, 2954, 2202, 1708, 1597, 1512, 1344, 1291, 1250/cm.

[α]_(D)=+27.4° (CHCl₃, c=0.53, 23° C.).

No. 1a-85

CDCl₃ 300 MHz

0.96-2.05(14H, m), 2.20 (1H, m), 2.3 5(2H, t, J=6.9 Hz), 2.99 (1H, m), 3.84(3H, s), 5.22-5.31(3H, m), 6.89(2H, d, J=8.7 Hz), 7.19(1H, brs), 7.29(1H, brs), 7.45-7.50(3H, m).

IR(CHCl₃): 3478, 3378, 3020, 2950, 2868, 2202, 1708, 1606, 1511, 1421, 1311, 1287, 1248, 1155/cm.

[α]_(D)=+17.1° (CHCl₃, c=1.00, 23° C.).

No. 1a-86

CDCl₃ 300 MHz

1.03-2.05(14H, m), 2.21(1H, m), 2.37(2H, t, J=6.9 Hz), 3.04(1H, m), 5.29-5.33(2H, m), 5.57(1H, d, J=6.3 Hz), 6.84-6.87(2H, m), 7.50-7.53(2H, m), 7.79(1H, d, J=8.1 Hz), 8.03(1H, d, d, J=1.5 and 8.1 Hz), 8.57(1H, d, J=1.5 Hz).

IR(CHCl₃): 3250, 3024, 2950, 2868, 2200, 1707, 1515, 1344, 1271, 1166, 1143/cm.

[α]_(D)=+21.22° (CHCl₃, c=0.26, 22° C.).

No. 1a-87

CD₃OD 300 MHz

1.04-2.00(14H, m), 2.18(1H, m), 2.26(2H, t, J=5.4 Hz), 2.93(1H, m), 5.19-5.24(2H, m), 6.77-6.80(2H, m), 7.05(1H, d.d, J=2.1 and 8.1 Hz), 7.22(1H, d, J=2.1 Hz), 7.38-7.42(3H, m).

IR(CHCl₃): 3377, 2952, 2873, 2204, 1705, 1607, 1515, 1425, 1312, 1267, 1222, 1153/cm.

[α]_(D)=−15.6° (CH₃OH, c=1.02, 22° C.).

No. 1a-88

CDCl₃ 300 MHz

0.90-1.96(14H, m), 2.22-2.31(3H, m), 2.95(1H, m), 3.65(3H, s), 4.87(1H, d, J=6.6 Hz), 5.13-5.28(2H, m), 7.46-7.62(3H, m), 7.82-7.89(4H, m), 7.90-7.96(2H, m), 2H, m) 8.42)1H, brs).

IR(CHCl₃): 3376, 3016, 2946, 2868, 1720, 1677, 1592, 1514, 1498, 1429, 1376, 1314, 1241, 1156, 1094/cm.

[α]_(D)=−10.7° (CHCl₃, c=1.04, 22.0° C.)

mp. 134-136° C.

No. 1a-89

CDCl₃+CD₃OD 300 MHz

0.96-2.08(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.2 Hz), 2.89(1H, m), 5.20-5.32(2H, m), 7.46-7.62(3H, m), 7.82-7.97(6H, m).

IR(KBr): 3272, 3007, 2952, 2874, 1708, 1660, 1592, 1527, 1498, 1433, 1400, 1317, 1260, 1152, 1094/cm.

[α]_(D)=−24.4° (CH₃OH, c=1.02, 25.0° C.).

No. 1a-90

CDCl₃ 300 MHz

0.89-1.96(14H, m), 2.23-2.33(3H, m), 2.92(1H, m), 3.67(3H, s), 4.85(1H, d, J=6.3 Hz), 5.10-5.25(2H, m), 7.81-7.90(4H, m), 8.10-8.18(2H, m), 8.31-8.40(2H, m), 8.77(1H, s),

IR(CHCl₃): 3372, 3018, 2946, 2868, 1718, 1685, 1592, 1527, 1436, 1397, 1346, 1318, 1256, 1154, 1099/cm.

[α]_(D)=−16.1° (CHCl₃, c=1.00, 23.0° C.).

No. 1a-91

CDCl₃+CD₃OD 300 MHz

0.94-2.02(14H, m), 2.18-2.36(3H, m), 2.87(1H, m), 5.15-5.30(2H, m), 7.82-7.92(4H, m), 8.09-8.16(2H, m), 8.30-8.37(2H, m).

IR(KBr): 3284, 3112, 3006, 2952, 2874, 1707, 1593, 1528, 1498, 1399, 1348, 1320, 1259, 1153, 1093/cm.

[α]_(D)=−26.3° (CH₃OH, c=1.01, 22° C.).

No. 1a-92

CDCl₃ 300 MHz

0.93-1.95(14H, m), 2.22-2.31(3H, m), 2.98(1H, m), 3.68(3H, s), 5.07(1H, d, J=6.9 Hz), 5.10-5.24(2H, m), 7.18(1H, m), 7.35-7.43(2H, m), 7.70(2H, d, J=7.8 Hz), 7.88-8.05(4H, m), 8.50(1H, brs).

IR(CHCl₃): 3382, 3008, 2952, 1720, 1675, 1599, 1525, 1499, 1438, 1321, 1253, 1161, 1087/cm.

[α]_(D)=−16.6° (CHCl₃, c=1.03, 24.0° C.)

mp. 100-101° C.

No. 1a-93

CDCl₃+CD₃OD 300 MHz

0.96-2.00(14H, m), 2.18-2.35(3H, m), 2.90(1H, m), 5.15-5.30(2H, m), 7.18(1H, m), 7.33-7.42(2H, m), 7.65-7.74(2H, m), 7.90-8.08(4H, m).

IR(KBr): 3347, 3194, 3011, 2955, 2875, 1706, 1650, 1602, 1544, 1499, 1443, 1325, 1265, 1165, 1091/cm.

[α]_(D)=−19.4° (CH₃OH, c=1.00, 24.0° C.)

mp. 158-159° C.

No. 1a-94

CD₃OD 300 MHz

1.05-2.00(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.98(1H, m), 3.80(3H, s), 5.13-5.27(2H, m), 6.88-6.98(2H, m), 7.54-7.64(2H, m), 7.94-8.12(4H, m).

IR(KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512, 1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090, 1032/cm.

[α]_(D)=−19.1° (CH₃OH, c=1.01, 24° C.).

No. 1a-95

CD₃OD 300 MHz

1.04-2.02(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.93-3.02(7H, m), 5.13-5.27(2H, m), 6.82-6.92(2H, m), 7.51-7.59(2H, m), 7.95-8.02(2H, m), 8.04-8.11(2H, m).

IR(KBr): 3370, 3006, 2953, 1708, 1649, 1604, 1541, 1512, 1460, 1441, 1414, 1328, 1302, 1248, 1162, 1107, 1090, 1032/cm.

[α]_(D)=−17.6° (CH₃OH, c=1.01, 24° C.).

No. 1a-96

CD₃OD 300 MHz

1.05-2.02(14H, m), 2.14(1H, m), 2.23(2H, t, J=7.2 Hz), 2.98(1H, m), 5.13-5.27(2H, m), 6.75-6.84(2H, m), 7.43-7.52(2H, m), 7.94-8.12(4H, m).

IR(KBr): 3339, 3197, 2953, 2875, 1707, 1644, 1606, 1541, 1514, 1446, 1325, 1293, 1259, 1240, 1225, 1161, 1091/cm.

[α]_(D)=−18.7° (CH₃OH, c=1.00, 24° C.).

mp. 193-196C.

No. 1a-97

d₆-DMSO 300 MHz

1.05-2.08(15H, m), 2.15(2H, t, J=7.5 Hz), 2.89(1H, m), 5.18-5.28(2H, m), 6.78-7.12(3H, m), 7.73(1H, d.d, J=1.4 and 7.8 Hz), 7.91-7.95(3H, m), 8.14(2H, d, J=8.4 Hz), 9.71(1H, s).

IR(KBr): 3407, 3191, 2953, 1711, 1646, 1614, 1603, 1537, 1457, 1326, 1162, 1151/cm.

[α]_(D)=−20.7° (CH₃OH, c=1.01, 21° C.).

No. 1a-98

CDCl₃ 300 MHz

0.93-2.00(14H, m), 2.21(1H, m), 2.31(2H, t, J=7.2 Hz), 2.93(1H, m), 3.84(3H, s), 3.85(6H, s), 5.15-5.30(2H, m), 5.45(1H, d, J=6.3 Hz), 7.04(2H, s), 7.78-7.86(2H, m), 7.90-7.98(2H, m), 8.58(1H, s).

IR(CHCl₃): 3264, 3008, 2954, 2874, 1707, 1670, 1607, 1537, 1506, 1451, 1421, 1308, 1158, 1129, 1088/cm.

[α]_(D)=−7.2° (CHCl₃, c=1.01, 23.5° C.).

mp. 147-149° C.

No. 1a-99

CD₃OD 300 MHz

1.04-1.98(14H, m), 2.21(1H, m), 2.10(2H, t, J=7.2 Hz), 2.95(1H, m), 3.76(3H, s), 3.86(6H, s), 5.07-5.24(2H, m), 7.19(2H, s), 7.99(2H, d, J=8.7 Hz), 8.13(1H, d, J=8.7 Hz).

IR(KBr): 3354, 3002, 2950, 2874, 1656, 1607, 1570, 1508, 1452, 1413, 1314, 1233, 1185, 1157, 1127, 1092/cm.

[α]_(D)=−20.3° (CH₃OH, c=1.00, 23.5° C.).

No. 1a-100

CDCl₃ 300 MHz

1.14-1.97(14H, m), 2.19(1H, m), 2.28(2H, t, J=7.4 Hz), 3.04(1H, m), 3.69(3H, s), 5.03(1H, d, J=6.9 Hz), 5.15-5.29(2H, m), 7.65(2H, d, J=8.4 Hz), 7.87(1H, s), 7.98(2H, d, J=8.4 Hz).

IR(CHCl₃): 3386, 3271, 3025, 3015, 2955, 2877, 1755, 1712, 1608, 1331, 1162/cm.

[α]_(D)=−29.4° (CH₃OH, c=1.01, 25° C.).

No. 1a-101

d₆-DMSO

1.00-2.20(17H, m), 2.84(1H, m), 5.00-5.20(2H, m), 7.78(2H, d, J=8.2 Hz), 7.84(1H, s), 7.89-7.95(3H, m).

IR(KBr): 3269, 3065, 3008, 2952, 2874, 2763, 1746, 1707, 1607, 1322, 1157/cm.

[α]_(D)=−26.2° (CH₃₀H, c=1.01, 25° C.).

No. 1a-102

CD₃OD

1.00-2.25(17H, m), 2.92(1H, s), 3.64(3H, s), 5.07-5.21(2H, m), 7.53(1H, s), 7.77(2H, d, J=8.6 Hz), 7.90(2H, d, J=8.6).

IR(KBr): 3430, 3277, 3006, 2952, 2873, 1720, 1687, 1620, 1571, 1438, 1312, 1156/cm.

[α]_(D)=−27.3° (CH₃OH, c=0.51, 26° C.),

mp 230-232° C.

No. 1a-103

CDCl₃ 300 MHz

0.94-1.96(14H, m), 2.19(1H, m), 2.28(2H, t, J=7.2 Hz), 3.04(1H, m), 3.69(3H, s), 5.11(1H,d,J=6.6 Hz), 5.15-5.28(2H, m), 7.60(2H, d, J=8.4 Hz), 7.67(1H, s), 7.98(2H, d, J=8.4 Hz).

IR(CHCl₃): 3381, 3021, 2955, 2876, 1735, 1605, 1437, 1411, 1325, 1231, 1177/cm.

[α]_(D)=+8.6° (CHCl₃, c=1.00, 23° C.).

No. 1a-104

CDCl₃ 300 MHz

0.94-1.96(14H, m), 2.21(1H, m), 2.31(2H, t, J=6.8 Hz), 2.99(1H, m), 5.18-5.28(2H, m), 5.45(1H, d, J=6.6 Hz), 7.61(2H, d, J=8.7 Hz), 7.67(1H, s), 7.99(2H, d, J=8.7 Hz).

IR(CHCl₃): 3382, 3222, 3028, 3019, 2957, 2876, 1736, 1709, 1604, 1412, 1322, 1301, 1286, 1179, 1162/cm.

[α]_(D)=+10.4° (CHCl₃, c=1.00, 23° C.).

No. 1a-105

CDCl₃ 300 MHz

0.92-1.98(14H, m), 2.17(1H, m), 2.26(2H. d, J=7.5 Hz), 3.01(1H, m), 3.69(3H, s), 4.01(3H, s), 4.84(1H, d, J=6.3 Hz), 5.14-5.30(2H, m), 7.71(2H, d, J=8.7 Hz), 7.87(2H, d, J=8.7 Hz), 8.09(1H, s).

IR(CHCl₃): 3385, 3284, 3025, 3015, 2954, 2877, 2821, 1730, 1598, 1459, 1438, 1403, 1341, 1160, 1052/cm.

[α]_(D)=+3.6° (CHCl₃, c=1.00, 26° C.).

No. 1a-106

CDCl₃ 300 MHz

0.92-2.08(14H, m), 2.14(1H, m), 2.34(2H, d, J=7.2 Hz), 3.02(1H, m), 4.01(3H, s), 5.19(1H, d, J=6.9 Hz), 5.23-5.32(2H, m), 7.71(2H, d, J=8.4 Hz), 7.88(2H, d, J=8.4 Hz), 8.09(1H, s).

IR(CHCl₃): 3510, 3384, 3268, 3028, 3021, 3014, 2957, 2877, 2821, 2667, 2821, 2666, 1707, 1598, 1459, 1404, 1341, 1324, 1160, 1052/cm.

[α]_(D)=+11.8° (CHCl₃, c=1.01, 25° C.).

mp 95-96° C.

No. 1a-107

CDCl₃ 300 MHz

0.92-1.97(14H, m), 1.34(3H, t, J=7.2 Hz), 2.18(1H, m), 2.28(2H. d, J=7.4 Hz), 3.01(1H, m), 3.68(3H, s), 4.26(2H, q, J=7.2 Hz), 4.86(1H, d, J=6.6 Hz), 5.15-5.29(2H, m), 7.71(2H, d, J=8.7 Hz), 7.87(2H, d, J=8.7 Hz), 8.09(1H, s).

IR(CHCl₃): 3385, 3282, 3025, 3026, 3015, 2954, 2877, 1729, 1599, 1480, 1458, 1438, 1403, 1338, 1161/cm.

[α]_(D)=+4.4° (CHCl₃, c=1.00, 25° C.).

No. 1a-108

CDCl₃ 300 MHz

0.90-2.04(14H, m), 1.34(3H, t, J=7.2 Hz), 2.14(1H, m), 2.34(2H, d, J=7.1 Hz), 3.01(1H, m), 4.27(2H, q, J=7.2 Hz), 5.20(1H, d, J=6.6 Hz), 5.21-5.35(2H, m), 7.71(2H, d, J=8.4 Hz), 7.88(2H, d, J=8.4 Hz), 8.10(1H, s).

IR(CHCl₃): 3514, 3384, 3270, 3025, 3015, 3015, 2957, 2877, 1708, 1599, 1458, 1403, 1324, 1324, 1160, 1050/cm.

[α]_(D)=+12.7° (CHCl₃, c=1.00, 25° C.).

No. 1a-109

[α]_(D)=+8.5° (CHCl₃, c=1.00, 25° C.).

mp 109.0-111.0° C.

No. 1a-110

CDCl₃: CD₃OD(95:5)

0.92-2.06(14H, m), 2.20(1H, m), 2.30(2H, d, J=7.2 Hz), 2.99(1H, m), 5.22-5.33(2H, m), 7.54-7.66(3H, m), 8.07(2H, d, J=9.0 Hz), 8.12-8.20(2H, m), 8.29(2H, d, J=9.0 Hz).

IR(Nujol): 3270, 2956, 2924, 2854, 1716, 1548, 1485, 1319, 1167/cm.

[α]_(D)=+17.0° (CHCl₃, c=1.00, 25° C.).

mp. 166.5-168° C.

No. 1a-111

[α]_(D)=+2.6° (CHCl₃, c=1.00, 24° C.).

mp120.0-121.0° C.

No. 1a-112

CDCl₃ 300 MHz

0.96-2.04(14H, m), 2.19(1H, m), 2.33(2H, d, J=7.1 Hz), 3.07(1H, m), 5.28-5.31(2H, m), 5.33(1H, d, J=6.6 Hz), 7.54-7.63(3H, m), 8.05(2H, d, J=8.4 Hz), 8.18-8.23(2H, m), 8.41 (2H, d, J=8.4 Hz).

IR(CHCl₃): 3384, 3269, 3025, 3015, 2957, 2877, 1708, 1598, 1496, 1457, 1417, 1326, 1164/cm.

[α]_(D)=+12.2° (CHCl₃, c=1.00, 24° C.).

mp. 163-164° C.

No. 1a-113

[α]_(D)=+22.1° (CHCl₃, c=1.05, 25° C.).

mp. 90-92C.

No. 1a-114

[C]_(D)=+2.2° (CHCl₃, c=1.02, 25° C.).

No. 1a-115

CDCl₃ 300 MHz

0.90-1.98(14H, m), 2.15-2.22(1H, m), 2.27(2H, t, J=7.2 Hz), 2.95-3.04(1H, m), 3.68(3H, s), 4.04(2H, s), 4.85(1H, d, J=6.6 Hz), 5.10-5.27(2H, m), 7.12-7.34(7H, m), 7.76-7.82(2H, m).

IR(CHCl₃): 3384, 3026, 2952, 1727, 1595, 1493, 1436, 1318, 1155, 1091, 890/cm.

[α]_(D)=0°

[α]₄₃₆=+4.9±0.4° (CHCl₃, c=1.05, 23° C.)

No. 1a-116

CDCl₃ 300 MHz

0.9-2.10(14H, m), 2.10-2.18(1H, m), 2.32(2H, t, J=7.2 Hz), 2.96-3.04(1H, m), 4.04(2H, s), 5.14(1H, d, J=6.6 Hz), 5.16-5.28(2H, m), 7.12-7.34(7H, m), 7.76-7.82(2H, m).

IR(CHCl₃): 3260, 3020, 2950, 1709, 1407, 1318, 1154, 1091, 892/cm.

[α]_(D)=+9.1±0.5° (CHCl_(3, c=)1.04, 23° C.)

No. 1a-117

CD₃OD 300 MHz

0.96-2.18(17H, m), 2.89-2.92(1H, m), 4.05(2H, s), 4.95-5.22(2H, m), 7.15-7.42(7H, m), 7.75-7.81(2H, m).

IR(KBr): 3429, 3279, 2951, 2872, 1563, 1494, 1453, 1408, 1313, 1155, 1093, 1057/cm.

[α]_(D)=−16.3±0.5° (CH₃OH, c=1.06, 25° C.)

No. 1a-118

CDCl₃ 300 MHz

0.98-1.70(15H, m), 1.80-2.00(5H, m), 2.20-2.40(3H, m), 2.98(1H, m), 4.06(2H, s), 4.72(1H, d, J=6.3 Hz), 5.00-5.23(3H, m), 7.16(2H, d, J=8.4 Hz), 7.26-7.33(5H, m), 7.79(2H, d, J=8.1 Hz).

IR(CHCl₃): 3376, 3020, 2948, 2868, 1716, 1596, 1492, 1453, 1407, 1318, 1155, 1105/cm.

[α]_(D)=+2.4° (CHCl₃, c=1.08, 24° C.).

No. 1a-119

CDCl₃ 300 MHz

0.90-2.02(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.00(1H, m), 3.68(3H, s), 4.86(1H, d, J=6.9 Hz), 5.13-5.34(2H, m), 7.00-7.09(4H, m), 7.22(1H, m), 7.37-7.45(2H, m), 7.79-7.86(2H, m).

IR(CHCl₃): 3376, 3018, 2946, 2868, 1727, 1582, 1486, 1321, 1243, 1151, 1093/cm.

[α]_(D)=+4.5° (CHCl₃, c=1.05, 23.5° C.).

No. 1a-120

CD₃OD 300 MHz

1.00-2.00(14H, m), 2.13(2H, t, J=7.5 Hz), 2.16(1H, m), 2.91(1H, m), 5.05-5.33(2H, m), 7.04-7.11(4H, m), 7.18-7.25(1H, m), 7.38-7.48(2H, m), 7.80-7.87(2H, m).

IR(KBr): 3430, 3278, 3006, 2952, 2873, 1583, 1487, 1410, 1322, 1298, 1245, 1152, 1095/cm.

[α]_(D)=−8.8° (CH₃OH, c=1.05, 25.0° C.).

No. 1a-121

CDCl₃ 300 MHz

0.90-2.10(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.2 Hz), 3.01(1H, m), 5.20(1H, d, J=6.9 Hz), 5.22-5.35(2H, m), 7.00-7.09(4H, m), 7.18-7.25(1H, m), 7.37-7.45(2H, m), 7.79-7.86(2H, m).

IR(CHCl₃): 3260, 3020, 2948, 2868, 1708, 1582, 1486, 1409, 1321, 1296, 1243, 1151, 1093/cm.

[α]_(D)=+13.1° (CHCl₃, c=1.04, 24.0° C.).

No. 1a-122

CDCl₃ 300 MHz

0.90-2.00(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.5 Hz), 2.96(1H, m), 3.67(3H, s), 4.69(1H, d, J=6.6 Hz), 5.15-5.32(2H, m), 6.22(1H, s), 6.98-7.40(5H, m), 7.30-7.38(2H, m), 7.68-7.74(2H, m).

IR(CHCl₃): 3416, 3370, 3018, 2946, 2868, 1725, 1587, 1508, 1437, 1400, 1320, 1149, 1094/cm.

[α]_(D)=+6.2° (CHCl₃, c=1.04, 25.0° C.).

No. 1a-123

CDCl₃ 300 MHz

0.90-2.04(14H, m), 2.18(1H, m), 2.33(2H, t, J=7.2 Hz), 2.96(1H, m), 5.04-5.35(3H, m), 6.98-7.12(3H, m), 7.12-7.20(2H, m), 7.28-7.38(2H, m), 7.66-7.74(2H, m).

IR(CHCl₃): 3424, 3270, 3028, 2952, 2872, 1708, 1587, 1508, 1445, 1399, 1320, 1148, 1092/cm.

[α]_(D)=+20.9° (CHCl₃, c=1.06, 23.0° C.).

No. 1a-124

CDCl₃ 300 MHz

0.90-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 3.00(1H, m), 3.14(3H, s), 3.68(3H, s), 4.56(2H, s), 4.84(1H, d, J=6.3 Hz), 5.10-5.29(2H, m), 7.16-7.26(4H, m), 7.26-7.34(2H, m), 7.78-7.84(2H, m).

IR(CHCl₃): 3384, 3028, 2952, 2874, 1727, 1598, 1501, 1435, 1410, 1370, 1329, 1172, 1148, 1091/cm.

[α]_(D)=+2.7° (CHCl₃, c=1.09, 23.0° C.).

No. 1a-125

CDCl₃ 300 MHz

0.90-2.00(14H, m), 2.18(1H, m), 2.28(2H, t, J=7.2 Hz), 2.29(3H, s), 3.00(1H, m), 3.68(3H, s), 4.04(2H, s), 4.80(1H, d, J=6.6 Hz), 5.11-5.29(2H, m), 6.99-7.06(2H, m), 7.12-7.19(2H, m), 7.31(2H, d, J=8.1 Hz), 7.79(2H, d, J=8.1 Hz).

IR(CHCl₃): 3382, 3280, 3024, 2950, 2874, 1730, 1596, 1504, 1435, 1407, 1367, 1318, 1196, 1155, 1091/cm.

[α]_(D)=+2.9° (CHCl₃, c=1.06, 23.0° C.).

No. 1a-126

CDCl₃ 300 MHz

0.90-2.02(14H, m), 2.14(1H, m), 2.29(3H, s), 2.32(2H, t, J=7.2 Hz), 3.01(1H, m), 4.03(2H, s), 5.10(1H, d, J=6.6 Hz), 5.15-5.30(2H, m), 6.98-7.06(2H, m), 7.11-7.18(2H, m), 7.30(2H, d, J=8.1 Hz), 7.79(2H, d, J=8.1 Hz).

IR(CHCl₃): 3374, 3260, 3020, 2948, 2868, 1749, 1708, 1596, 1504, 1407, 1369, 1317, 1195, 1155, 1091/cm.

[α]_(D)=+10.0° (CHCl₃, c=1.09, 23.0° C.).

No. 1a-127

CDCl₃ 300 MHz

0.87-1.95(14H, m), 2.18-2.32(3H, m), 2.95(1H, m), 3.69(3H, s), 3.96(2H, s), 4.79(1H, d, J=6.6 Hz), 4.97-5.17(2H, m), 5.54(1H, s), 6.75-6.82(2H, m), 6.97-7.05(2H, m), 7.25-7.33(2H, m), 7.75-7.81(2H, m).

IR(CHCl₃): 3382, 3026, 2950, 2874, 1722, 1595, 1511, 1436, 1407, 1317, 1257, 1154, 1090/cm.

[α]_(D)=−2.1° (CHCl₃, c=1.00, 21.5° C.).

No. 1a-128

CDCl₃ 300 MHz

0.8 5-2.02 (14H, m), 2.18 (1H, m), 2.31 (2H, t, J=7.2 Hz), 2.96(1H, m), 3.95(2H, s), 5.05-5.27(3H, m), 6.73-6.82(2H, m), 6.96-7.04(2H, m), 7.25-7.32(2H, m), 7.74-7.81(2H, m).

IR(CHCl₃): 3262, 3020, 2948, 2868, 1708, 1596, 1511, 1407, 1315, 1242, 1154, 1091/cm.

[α]_(D)=+4.8° (CHCl₃, c=1.04, 22° C.).

No. 1a-129

CDCl₃ 300 MHz

0.89-1.98(14H, m), 2.18(1H, m), 2.27(2H, t, J=7.2 Hz), 2.99(1H, m), 3.68(3H, s), 3.79(3H, s), 3.98(2H, s), 4.81(1H, d, J=6.6 Hz), 5.10-5.27(2H, m), 6.81-6.87(2H, m), 7.03-7.10(2H, m), 7.25-7.32(2H, m), 7.75-7.82(2H, m).

IR(CHCl₃): 3382, 3276, 3006, 2950, 2874, 1726, 1609, 1509, 1457, 1436, 1407, 1315, 1244, 1154, 1091, 1033/cm.

[α]_(D)=+19.3° (CHCl₃, c=1.05, 23° C.).

No. 1a-130

CDCl₃ 300 MHz

0.90-2.00(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.2 Hz), 2.98(1H, m), 3.69(3H, s), 4.81(1H, d, J=6.6 Hz), 5.12-5.32(2H, m), 5.46(1H, brs), 6.84-7.01 (6H, m), 7.76-7.83(2H, m)

IR(CHCl₃): 3380, 3284, 3024, 2952, 2874, 1724, 1588, 1504, 1488, 1436, 1321, 1296, 1149, 1091/cm.

[α]_(D)=+28.9° (CHCl₃, c=1.01, 23° C.).

No. 1a-131

CDCl₃ 300 MHz

0.92-2.10(14H, m), 2.18(1H, m), 2.34(2H, t, J=6.9 Hz), 2.96(1H, m), 5.18-5.35(3H, m), 6.84-7.01(6H, m), 7.75-7.83(2H, m).

IR(CHCl₃): 3270, 3028, 2952, 2874, 1708, 1589, 1505, 1489, 1456, 1322, 1297, 1238, 1148, 1091/cm.

[α]_(D)=+7.7° (CHCl₃, c=1.09, 24° C.).

No. 1a-132

CDCl₃ 300 MHz

0.91-2.02(14H, m), 2.19(1H, m), 2.29(2H, t, J=7.2 Hz), 2.99(1H, m), 3.68(3H, s), 3.83(3H, s), 4.82(1H, d, J=6.6 Hz), 5.14-5.33(2H, m), 6.90-7.04(6H, m), 7.76-7.83(2H, m).

IR(CHCl₃): 3384, 3006, 2952, 2874, 1727, 1589, 1502, 1488, 1459, 1438, 1321, 1295, 1231, 1150, 1092, 1033/cm.

[α]_(D)=+3.1° (CHCl₃, c=1.01, 23° C.).

No. 1a-133

TLC Rf=0.21 (ethyl acetate/n-hexane=1:1 (0.3% acetic acid))

No. 1a-134

CDCl₃ 300 MHz

0.97-2.10(14H, m), 2.20(1H, m), 2.36(2H, t, J=6.9 Hz), 3.04(1H, m), 5.22-5.33(2H, m), 5.41(1H, d, J=6.6 Hz), 7.02(1H, d, J=9.0 Hz), 7.09-7.13(2H, m), 7.26-7.32(1H, m), 7.43-7.49(2H, m), 7.93(1H, d.d, J=2.4 and 9.0 Hz), 8.46(1H, d, J=2.4 Hz).

IR(CHCl₃): 3384, 3270, 3020, 2958, 1709, 1610, 1587, 1537, 1479, 1352, 1271, 1252, 1167/cm.

[α]_(D)=+20.9° (CHCl₃, c=0.51, 22° C.).

No. 1a-135

CDCl₃ 300 MHz

0.96-2.02(14H, m), 2.21(1H, m), 2.29(2H, t, J=7.2 Hz), 3.07(1H, m), 3.68(3H, s), 5.04(1H, d, J=6.9 Hz), 5.16-5.33(2H, m), 7.48-7.55(2H, m), 7.64(1H, m), 7.76-7.82(2H, m), 7.88-7.94(2H, m), 7.98-8.04(2H, m).

IR(CHCl₃): 3384, 3282, 3026, 2952, 2874, 1727, 1663, 1596, 1446, 1396, 1316, 1274, 1163, 1090/cm.

[α]_(D)=+3.1° (CHCl₃, c=1.03, 22.0° C.).

No. 1a-136

CDCl₃ 300 MHz

0.95-2.05(14H, m), 2.19(1H, m), 2.34(2H, t, J=7.2 Hz), 3.08(1H, m), 5.10-5.40(2H, m), 5.35(1H, d, J=6.8 Hz), 7.45-7.58(2H, m), 7.64(1H, m), 7.74-7.84(2H, m), 7.84-7.95(2H, m), 7.95-8.06(2H, m).

IR(CHCl₃): 3260, 3018, 2950, 2870, 1708, 1662, 1595, 1446, 1395, 1316, 1274, 1162, 1090/cm.

[α]_(D)=+12.9° (CHCl₃, c=1.05, 21.5° C.).

No. 1a-137

CDCl₃ 300 MHz

0.97-2.04(14H, m), 2.27(1H, m), 2.31(2H, t, J=7.2 Hz), 3.07(1H, m), 3.70(3H, s) 5.15-5.30(3H, m), 7.48-7.68(5H, m), 7.96-8.02(2H, m).

IR(CHCl₃): 3382, 3030, 2952, 2878, 1725, 1446, 1329, 1154, 1098/cm.

[α]_(D)=−12.1° (CHCl₃, c=1.03, 22.0° C.).

No. 1a-138

CDCl₃ 300 MHz

0.95-2.04(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.2 Hz), 3.08(1H, m), 5.15-5.34(2H, m), 5.41(1H, d, J=6.6 Hz), 7.48-7.68(5H, m), 7.98-8.03(2H, m).

IR(CHCl₃): 3370, 3242, 3022, 2950, 2870, 1707, 1445, 1408, 1329, 1154, 1099/cm.

[α]_(D)=−0.6° (CHCl₃, c=1.06, 21.5° C.) [α]₃₆₅+30.7° (CHCl₃, c=1.06, 21.5° C.)

No. 1a-139

CDCl₃ 300 MHz

0.92-2.19(14H, m), 2.27-2.34(3H, m), 3.26(1H, m), 3.65(3H, s), 4.28(2H, s), 4.37(1H, d, J=7.4 Hz), 5.34-5.50(2H, m), 7.37-7.62(9H, m).

IR(CHCl₃): 3389, 3294, 3028, 3015, 2954, 2877, 1730, 1600, 1488, 1325, 1151, 1129/cm.

[α]_(D)=−24.8° (CHCl₃, c=1.01, 24° C.).

No. 1a-140

CDCl₃ 300 MHz

0.92-2.22(15H, m), 2.34(2H, t, J=7.1 Hz), 3.24(1H, m), 4.29(2H, s), 4.81(1H, d, J=7.4 Hz), 5.32-5.52(2H, m), 7.36-7.62(9H, m).

IR(CHCl₃): 3510, 3388, 3251, 3031, 3015, 2956, 2877, 2668, 1708, 1601, 1488, 1318, 1151, 1129/cm.

[α]_(D)=−24.6° (CHCl₃, c=1.02, 25° C.).

No. 1a-141

CDCl₃ 300 MHz

0.92-2.19(15H, m), 2.32(2H, t, J=7.2 Hz), 3.26(1H, m), 3.65(3H, s), 4.31(2H, s), 4.48(1H, d, J=7.4 Hz), 5.33-5.49(2H, m), 7.42-7.80(8H, m).

IR(CHCl₃): 3388, 3285, 3018, 2955, 2877, 2225, 1730, 1597, 1479, 1320, 1152, 1129/cm.

[α]_(D)=−20.1° (CHCl₃, c=0.96, 25° C.).

No. 1a-142

CDCl₃ 300 MHz

0.92-2.22(15H, m), 2.35(2H, t, J=6.8 Hz), 3.25(1H, m), 4.32(2H, s), 4.86(1H, d, J=7.4 Hz), 5.33-5.53(2H, m), 7.43-7.80(8H, m).

IR(CHCl₃): 3512, 3388, 3258, 3031, 3023, 3014, 2956 2877, 2225, 1708, 1597, 1479, 1319, 1151, 1128/cm.

[α]_(D)=−19.3° (CHCl₃, c=1.09, 23° C.).

No. 1a-143

CDCl₃ 300 MHz

1.00-1.93(14H, m), 2.17(1H, m), 2.27(2H, t, J=7.2 Hz), 3.07(1H, m), 5.17-5.22(2H, m), 5.36(1H, d, J=6.9 Hz), 7.77(1H, d, J=9.0 Hz), 8.11-8.17(2H, m), 8.36(1H, d.d, J=2.1 and 9.0 Hz), 8.51(1H, d, J=1.8 Hz), 8.65(1H, d, J=2.1 Hz).

IR(CHCl₃): 3382, 3266, 3026, 2954, 2874, 1708, 1632, 1585, 1528, 1458, 1419, 1345, 1153/cm.

[α]_(D)=+7.6° (CHCl₃, c=1.04, 22° C.).

No. 1a-144

CDCl₃ 300 MHz

0.95-1.90(14H, m), 2.17(1H, m), 2.25(2H, t, J=7.5 Hz), 3.02(1H, m), 5.09(1H, d, J=6.6 Hz), 5.15 5.21(2H, m), 6.72(1H, d, J=8.4 Hz), 6.85(1H, s), 7.54(1H, d, J=8.4 Hz), 7.72(1H, d, J=9.0 Hz), 7.83(1H, d.d, J=1.8 and 9.0 Hz), 8.32(1H, d, J=1.8 Hz).

IR(CHCl₃): 3380, 3260, 3022, 2948, 2868, 2352, 1709, 1636, 1460, 1425, 1313, 1291, 1265, 1148, 1130/cm.

[α]_(D)=+12.9° (CHCl, c=1.02, 22.5° C.).

No. 1a-145

CDCl₃ 300 MHz

0.97-1.90(14H, m), 2.15(1H, m), 2.27(2H, t, J=6.9 Hz), 3.02(1H, m), 3.08(6H, s), 5.12(1H, d, J=6.3 Hz), 5.19-5.25(2H, m), 6.78-6.84(2H, m), 7.53(1H, d, J=8.7 Hz), 7.76-7.83(2H, m), 8.30(1H, d, J=1.8 Hz).

IR(CHCl₃): 3272, 3030, 2950, 2874, 1708, 1635, 1601, 1511, 1457, 1425, 1357, 1328, 1151, 1124/cm.

[α]_(D)=+6.3° (CHCl₃, c=1.04, 23° C.).

No. 1a-146

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.16(1H, m), 2.29(2H, t, J=7.2 Hz), 3.05(1H, m), 4.10(3H, s), 5.12-5.28(2H, m), 5.38(1H, d, J=6.9 Hz), 7.67-7.74(2H, m), 8.08(1H, d.d, J=1.8 and 9.0 Hz), 8.11(1H, s), 8.61(1H, d, J=1.8 Hz).

IR(CHCl₃): 3260, 3020, 2948, 2868, 1708, 1639, 1606, 1528, 1470, 1455, 1424, 1349, 1311, 1238, 1174, 1149, 1120, 1079, 1060, 1022/cm.

[α]_(D)=+7.8° (CHCl₃, c=1.00, 23° C.).

No. 1a-147

CDCl₃ 300 MHz

0.92-1.92(14H, m), 2.17(2H, m), 2.25(2H, t, J=7.2 Hz), 3.01(1H, m), 3.97(3H, s), 5.10-5.27(5H, m), 6.92(1H, s), 7.29(1H, s), 7.52(1H, d, J=8.7 Hz), 7.82(1H, d.d, J=2.1 and 8.7 Hz), 8.33(1H, d, J=2.1 Hz).

IR(CHCl₃): 3380, 3264, 3002, 2950, 2868, 1708, 1634, 1476, 1452, 1426, 1317, 1264, 1218, 1169, 1147, 1115, 1068, 1031/cm.

[α]_(D)=+5.6° (CHCl₃, c=1.02, 23° C.).

No. 1a-148

CDCl₃ 300 MHz

0.90-1.98(14H, m), 2.15(1H, m), 2.28(2H, t, J=6.9 Hz), 2.91(6Hs), 3.03(1H, m), 4.01(3H, s), 5.15-5.26(3H, m), 7.18(1H, s), 7.38(1H, s), 7.59(1H, d, J=8.7 Hz), 7.87(1H, d.d, J=2.1 and 8.7 Hz), 8.40(1H, d, J=2.1 Hz).

IR(CHCl₃): 3384, 3266, 2956, 1709, 1632, 1602, 1495, 1473, 1458, 1430, 1317, 1231, 1148, 1121/cm.

[α]_(D)=+11.2° (CHCl₃, c=1.01, 23° C.).

No. 1a-149

CDCl₃ 300 MHz

0.99-1.90(14H, m), 2.17(1H, m), 2.28(2H, t, J=7.2 Hz), 3.00(1H, m), 5.13-5.19(2H, m), 5.43(1H, d, J=6.0 Hz), 7.02(1H, d.d, J=2.4 and 9.0 Hz), 7.38-7.41(2H, m), 7.58(1H, d, J=8.7 Hz), 7.96(1H, d.d, J=1.8 and 8.7 Hz), 8.45(1H, d, J=1.8 Hz).

IR(CHCl₃): 3270, 3020, 2948, 2868, 1709, 1601, 1478, 1448, 1419, 1315, 1147, 1120/cm.

[α]_(D)=−11.4° (CHCl₃, c=1.01, 23° C.).

No. 1a-150

CDCl₃ 300 MHz

0.97-1.88(14H, m), 2.12-2.31(3H, m), 2.38(3H, s), 3.01(1H, m), 5.14-5.19(2H, m), 5.36(1H, d, J=6.6 Hz), 7.24(1H, d.d, J=2.4 and 9.0 Hz), 7.59(1H, d, J=6.3 Hz), 7.66(1H, d, J=8.7 Hz), 7.72(1H, d, J=2.4 Hz), 8.01(1H, d.d, J=1.8 and 8.7 Hz), 8.49(1H, d, J=1.8 Hz).

IR(CHCl₃): 3470, 3374, 3260, 3018, 2950, 2868, 1709, 1474, 1444, 1412, 1370, 1319, 1266, 1162, 1145, 1118/cm.

[α]_(D)=+4.9° (CHCl₃, c=1.00, 24° C.).

No. 1a-151

CDCl₃ 300 MHz

0.97-1.89(14H, m), 2.17(1H, m), 2.25(2H, t, J=7.2 Hz), 3.03(1H, m), 3.92(3H, s), 5.15-5.20(2H, m), 5.32(1H, d, J=6.6 Hz), 7.11(1H, d.d, J=2.4 and 9.3 Hz), 7.45(1H, d, J=2.4 Hz), 7.50(1H, d, J=9.3 Hz), 7.62(1H, d, J=8.7H), 7.97(1H, d.d, J=2.1 and 8.7 Hz), 8.50(1H, d, J=2.1 Hz).

IR(CHCl₃): 3260, 3018, 2948, 1708, 1483, 1454, 1432, 1314, 1287, 1268, 1188, 1169, 1147/cm.

[α]_(D)=+4.9° (CHCl₃, c=1.01, 23.5° C.).

No. 1a-152

CDCl₃ 300 MHz

0.98-2.04(14H, m), 2.15(1H, m), 2.30(2H, t, J=6.6 Hz), 3.04(1H, m), 5.17-5.29(3H, m), 7.41(1H, d.d, J=1.5 and 8.1 Hz), 7.64-7.68(2H, m), 7.92(1H, d, J=8.4 Hz), 8.00(1H, d.d, J=1.8 and 8.4 Hz), 8.49(1H, d, J=1.8 Hz).

IR(CHCl₃): 3266, 3028, 2952, 2872, 1707, 1629, 1591, 1456, 1416, 1318, 1275, 1150/cm.

[α]_(D)=+3.2° (CHCl₃, c=1.04, 23° C.).

No. 1a-153

CDCl₃ 300 MHz

0.97-1.88(14H, m), 2.16(1H, m), 2.26(2H, t, J=7.2 Hz), 3.03(1H, m), 4.64-4.65(2H, m), 5.16-5.50(5H, m), 6.13(1H, m), 7.14(1H, d.d, J=2.7 and 9.0 Hz), 7.46-7.52(2H, m), 7.63(1H, d, J=8.7 Hz), 7.97(1H, d.d, J=1.8 and 8.7 Hz), 8.49(1H, d, J=1.8 Hz).

IR(CHCl₃): 3374, 3260, 3020, 2948, 2868, 1708, 1599, 1478, 1446, 1414, 1314, 1284, 1268, 1184, 1148, 1120/cm.

[α]_(D)=+5.3° (CHCl₃, c=1.00, 23° C.).

No. 1a-154

CDCl₃ 300 MHz

0.99-2.00(15H, m), 2.26(2H, t, J=7.2 Hz), 3.03(1H, m), 4.07(3H, s), 5.23-5.27(2H, m), 5.36(1H, d, J=7.2 Hz), 7.20(1H, s), 7.36-7.48(2H, m), 7.55-7.58(1H, m), 7.91-7.93(1H, m), 8.52(1H, s).

IR(CHCl₃): 3362, 3257, 3020, 2948, 2868, 1708, 1637, 1602, 1579, 1488, 1457, 1437, 1413, 1345, 1318, 1301, 1276, 1182, 1104/cm.

[α]_(D)=+19.4° (CHCl₃, c=1.01, 25° C.).

mp. 88-90° C.

No. 1a-155

CDCl₃ 300 MHz

0.92-2.02(14H, m), 2.15(1H, m), 2.31(2H, t,, J=7.2 Hz), 3.01(1H, m), 4.10(2H, s), 5.10(1H, d, J=6.6 Hz), 5.18-5.35(2H, m), 7.04-7.26(5H, m), 7.67-7.76(2H, m).

IR(CHCl₃): 3266, 3028, 2952, 2952, 2872, 1708, 1599, 1574, 1478, 1457, 1418, 1301, 1258, 1147, 1124, 1101, 1080/cm.

[α]₃₆₅ +33.4° (CHCl₃, c=1.00, 23° C.).

No. 1a-156

CDCl₃ 300 MHz

0.91-2.21(15H, m), 2.33(2H, t, J=6.9 Hz), 3.01(1H, m), 5.11(1H, d, J=6.6 Hz), 5.27-5.35(2H, m), 6.85-6.96(5H, m), 7.35(1H, d, J=2.1 Hz), 7.42(1H, d.d, J=2.1 and 8.7 Hz).

IR(CHCl₃): 3384, 3263, 2957, 1708, 1587, 1489, 1462, 1416, 1290, 1222, 1151, 1123/cm.

[α]_(D)=+6.4° (CHCl₃, c=1.00, 23° C.).

No. 1a-157

CDCl₃ 300 MHz

0.97-1.91(14H, m), 2.18(1H, m), 2.26(2H, t, J=6.9 Hz), 3.04(1H, m), 5.18-5.26(3H, m), 7.52-7.56(2H, m), 7.88-8.00(3H, m), 8.25(1H, m), 8.69(1H, m).

IR(CHCl₃): 3382, 3268, 2952, 2874, 1707, 1457, 1425, 1409, 1318, 1152/cm.

[α]_(D)=+4.4° (CHCl₃, c=1.02, 22° C.).

No. 1a-158

CDCl₃ 300 MHz

1.02-1.97(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.2 Hz), 3.06(1H, m), 5.19-5.24(2H, m), 5.58(1H, d, J=6.6 Hz), 7.62(1H, m), 7.72(1H, m), 7.86-7.91(2H, m), 7.96(1H, d, J=7.8 Hz), 8.04(1H, d.d, J=1.5 and 8.1 Hz), 8.34(1H, d, J=1.2 Hz).

IR(CHCl₃): 3490, 3260, 3020, 2950, 2870, 1707, 1456, 1399, 1³12, 1165/cm.

[α]_(D)=−8.3° (CHCl₃, c=1.00, 23° C.).

No. 1a-159

CDCl₃ 300 MHz

0.92-1.88(14H, m), 2.13(1H, m), 2.24(2H, m), 3.02(1H, m), 3.90(3H, s), 5.12-5.26(3H, m), 7.29-7.58(4H, m), 7.97(1H, d.d, J=1.8 and 7.5 Hz), 8.13(1H, d, J=7.5 Hz), 8.64(1H, d, J=1.8 Hz).

IR(CHCl₃): 3382, 3266, 3018, 2956, 1708, 1629, 1594, 1476, 1467, 1325, 1245, 1227, 1158, 1146/cm.

[α]_(D)=+14.6° (CHCl₃, c=1.00, 22° C.).

No. 1a-160

CDCl₃ 300 MHz

0.93-1.88(14H, m), 2.18-2.24(3H, m), 3.00(1H, m), 5.08-5.21(3H, m), 7.28-7.33(1H, m), 7.47-7.51(3H, m), 7.90(1H, d.d, J=1.5 and 7.8 Hz), 8.10(1H, d, J=7.8 Hz), 8.63-8.64(2H, m).

IR(CHCl₃): 3465, 3380, 3275, 3020, 2957, 2876, 1708, 1627, 1604, 1495, 1473, 1457, 1328, 1240, 1222, 1156, 1149/cm.

[α]_(D)=+8.2° (CHCl₃, c=1.01, 22° C.).

No. 1a-161

CDCl₃ 300 MHz

0.98-1.88(14H, m), 2.17(1H, m), 2.24(2H, t, J=7.2 Hz), 3.05(1H, m), 5.16-5.20(2H, m), 5.35(1H, d, J=6.6 Hz), 7.40(1H, m), 7.55(1H, m), 7.63(1H, d, J=8.1 Hz), 7.89(1H, d.d, J=1.5 and 8.1 Hz), 8.01(1H, m), 8.06(1H, d, J=8.1 Hz), 8.12(1H, d, J=1.5 Hz).

IR(CHCl₃): 3478, 3266, 3028, 2952, 2874, 1708, 1454, 1417, 1323, 1196, 1148/cm.

[α]_(D)=+21.9° (CHCl₃, c=1.01, 23° C.).

No. 1a-162

CDCl₃ 300 MHz

0.96-1.98(14H, m), 2.02(1H, m), 2.25(2H, t, J=7.2 Hz), 3.05(1H, m), 4.10(3H, s), 5.14-5.25(2H, m), 5.41(1H, d, J=7.2 Hz), 7.35-7.42(1H, m), 7.51-7.64(3H, m), 7.94-8.00(1H, m), 8.16(1H, s).

IR(CHCl₃): 3368, 3274, 3028, 2952, 2874, 1708, 1633, 1583, 1465, 1452, 1438, 1413, 1315, 1151, 1103, 1053, 1024/cm.

[α]_(D)=+15.1° (CHCl₃, c=1.01, 23° C.).

mp. 108-110° C.

No. 1a-163

d₆-DMSO 300 MHz

0.97-1.84(14H, m), 1.92(1H, m), 2.04(2H, t, J=7.5 Hz), 2.90(1H, m), 5.08-5.23(2H, m), 7.32(1H, s), 7.38-7.61(2H, m), 7.62(1H, s) 7.68-7.71(1H, m), 7.92(1H, s), 8.14-8.17(1H, m), 10.7(1H, s), 11.9(1H, s).

IR(KBr): 3350, 3295, 2952, 2874, 1707, 1636, 1601, 1466, 1431, 1389, 1315, 1251, 1174, 1146, 1106/cm.

[α]_(D)=−25.3° (CH₃OH, c=1.01, 25° C.).

mp. 159-162° C.

No. 1a-164

CDCl₃ 300 MHz

0.98-1.96(17H, m), 2.05(1H, m), 2.25(2H, t, J=7.2 Hz), 3.07(1H, m), 4.32(2H, q, J=7.2 Hz), 5.19-5.23(2H, m), 5.31(1H, d, J=7.8 Hz), 7.38(1H, m), 7.41-7.62(3H, m), 7.95(1H, m), 8.15(1H, s).

IR(CHCl₃): 3360, 3018, 2946, 2870, 1709, 1633, 1457, 1445, 1425, 1394, 1314, 1176, 1152, 1105/cm.

[α]_(D)=+12.7° (CHCl₃, c=1.02, 25° C.).

mp. 108-109° C.

No. 1a-165

CDCl₃ 300 MHz

0.95-1.98(15H, m), 2.26(2H, t, J=7.5 Hz), 3.04(1H, m), 4.15(3H, s), 5.20-5.26(2H, m), 5.34(1H, d, J=6.9 Hz), 7.41-7.47(1H, m), 7.65-7.68(2H, m), 7.89-7.92(1H, m), 8.32(1H, s).

IR(CHCl₃): 3366, 3087, 3022, 2957, 1708, 1632, 1538, 1463, 1408, 1364, 1346, 1308, 1227, 1212, 1205, 1167/cm.

[α]_(D)=+19.6° (CHCl₃, c=1.01, 25° C.).

No. 1a-166

CDCl₃ 300 MHz

0.97-2.02(15H, m), 2.27(2H, t, J=6.9 Hz), 3.07(1H, m), 4.14(3H, s), 5.21-5.27(2H, m), 5.47(1H, d, J=6.9 Hz), 7.64(1H, s), 7.72(1H, d.d, J=0.6 and 9.0 Hz), 8.25(1H, s), 8.47(1H, d.d, J=2.4 and 9.0 Hz), 8.94(1H, d.d, J=0.6 and 2.4 Hz).

IR(CHCl₃): 3373, 2957, 1708, 1639, 1587, 1528, 1467, 1428, 1415, 1345, 1221, 1184, 1155/cm.

[α]_(D)=+14.4° (CHCl₃, c=0.50, 25° C.)

No. 1a-167

CDCl₃ 300 MHz

0.92-2.00(14H, m), 2.15(1H, m), 2.27(2H, t, J=7.2 Hz), 3.04(1H, m), 3.97(2H, s), 5.15-5.30(3H, m), 7.35-7.47(2H, m), 7.55-7.63(1H, m), 7.80-7.96(3H, m), 8.05(1H, d, J=0.3 Hz).

IR(CHCl₃): 3260, 3020, 2948, 2868, 1707, 1451, 1413, 1319, 1172, 1144, 1101, 1071/cm.

[α]_(D)=+18.2° (CHCl₃, c=1.04, 22° C.).

No. 1a-168

CDCl₃ 300 MHz

0.90-1.88(14H, m), 2.16(1H, m), 2.25(2H, t, J=6.9 Hz), 3.00(1H, m), 5.00-5.19(2H, m), 5.3 5 (H, d, J=6.6 Hz), 7.2 5-7.30 (1H, m), 7.4 8-7.50(2H, m), 7.73 (1H, d.d, J=1.5 and 8.1 Hz), 8.08-8.14(3H, m), 8.93(1H, s).

IR(CHCl₃): 3466, 3380, 3276, 3016, 2957, 1708, 1630, 1495, 1458, 1324, 1241, 1150/cm.

[α]_(D)=+18.0° (CHCl₃, c=1.00, 22° C.).

No. 1a-169

CDCl₃ 300 MHz

0.87-1.86(14H, m), 2.15(1H, m), 2.25(2H, t, J=6.9 Hz), 2.98(1H, m), 3.89(3H, s), 5.00-5.22(2H, m), 5.27(1H, d, J=6.9 Hz), 6.88(1H, d.d, J=2.1 and 8.4 Hz), 6.94(1H, d, J=2.1 Hz), 7.69(1H, d.d, J=1.5 and 7.8 Hz), 7.92-8.01(3H, m), 8.83(1H, s).

IR(CHCl₃): 3465, 3378, 3276, 3022, 2957, 1708, 1630, 1609, 1569, 1459, 1433, 1314, 1281, 1229, 1151/cm.

[α]_(D)=+19.3° (CHCl₃, c=1.01, 21° C.).

No. 1a-170

CDCl₃ 300 MHz

0.88-2.25(17H, m), 3.04(1H, m), 3.84(3H, s), 3.95(3H, s), 5.06-5.26(3H, m), 6.87-6.93(2H, m), 7.69(1H, d.d, J=1.6 and 8.2 Hz), 7.93-9.05(3H, m).

IR(CHCl₃): 3026, 2957, 1708, 1630, 1601, 1460, 1331, 1243, 1224, 1152/cm.

[α]_(D)=+17.2° (CHCl₃, c=1.00, 22° C.).

No. 1a-171

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.16-2.32(3H, m), 2.66(3H, s), 3.14(1H, m), 3.68(3H, s), 5.09(1H, d, J=6.8 Hz), 5.10-5.28(2H, m), 7.45(1H, d.d., J=1.8&8.6 Hz), 7.75-7.84(2H, m).

IR(CHCl₃): 3374, 3018, 2946, 2868, 1725, 1585, 1513, 1436, 1340, 1278, 1153, 1112/cm.

[α]_(D)=−14.7° (CHCl₃, c=1.07, 25.0° C.).

No. 1a-172

CDCl₃ 300 MHz

0.97-2.02(14H, m), 2.23(1H, m), 2.28(2H, t, J=7.2 Hz), 2.66(3H, s), 3.14(1H, m), 5.12-5.22(2H, m), 5.41(1H, d, J=7.2 Hz), 7.45(1H, d.d., J=2.1&8.7 Hz), 7.76(1H, d, J=8.7 Hz), 7.78(1H, d, J=2.1 Hz).

IR(CHCl₃): 3372, 3250, 3022, 2950, 2868, 1707, 1514, 1419, 1336, 1279, 1154, 1112/cm.

[α]_(D)=−4.1° (CHCl₃, c=1.08, 26.0° C.)

m.p.141-143° C.

No. 1a-173

CDCl₃ 300 MHz

1.15-2.42(17H, m), 2.91(1H, m), 5.15(1H, d, J=4.2 Hz), 5.25-5.40(2H, m), 7.85(1H, d, J=7.2 Hz), 8.00(1H, t, J=8.1 Hz), 8.15-8.20(2H, m), 8.67(1H, d, J=8.1 Hz), 8.73(1H, d, J=8.1 Hz), 8.83(1H, s), 9.43(1H, s).

IR(KBr): 3422, 3269, 3046, 2952, 2871, 1711, 1617, 1447, 1333, 1243, 1161, 1146/cm.

[α]_(D)=−41.0° (CH, OH, c=1.01, 23° C.).

No. 1a-174

CDCl₃+d₆-DMSO 300 MHz

1.00-1.92(14H, m), 2.20(2H, t, J=6.6 Hz), 2.35(1H, m), 2.92(1H, m), 5.05-5.22(2H, m), 6.63(1H, d, J=5.4 Hz), 7.77-7.92(3H, m), 8.31(1H, d.d, J=1.8 and 8.7 Hz), 8.59(1H, d, J=8.7 Hz), 8.73(1H, d, J=8.7 Hz), 9.01(1H, s), 9.55(1H, d, J=1.8 Hz).

IR(KBr): 3433, 3252, 2952, 2871, 1696, 15 78, 1423, 1335, 1308, 1219, 1185, 1160, 1106/cm.

[α]_(D)=−19.3° (DMSO, c=0.50, 23° C.).

No. 1a-175

CDCl₃ 300 MHz

0.96-1.87(14H, m), 2.20-2.25(3H, m), 2.95(1H, m), 3.66(3H, s), 4.74(1H, d, J=6.6 Hz), 5.10-5.12(2H, m), 6.88(1H, d, J=1.2 Hz), 7.37-7.50(3H, m), 7.56(1H, dd, J=8.7 1.5 Hz), 7.68-7.77(3H, m), 8.06(1H, s), 9.44(1H, dd, J=1.2 Hz).

IR(CHCl₃): 3462, 3374, 3026, 3006, 2952, 2872, 1724, 1610, 1580, 1484, 1452, 1358, 1309, 1147.

[α]_(D)=+16.4° (CHCl₃, c=1.05, 26° C.).

mp. 130-132° C.

No. 1a-176

CDCl₃+CD₃OD 300 MHz

1.00-2.02(14H, m), 2.22(1H, m), 2.29(2H, t, J=6.9 Hz), 2.88(1H, m), 5.16-5.26(2H, m), 6.87(1H, s), 7.28-7.57(4H, m), 7.69(1H, d, J=8.4 Hz), 7.75-7.78(2H, m), 7.99(1H, s).

IR(KBr): 3254, 2944, 1704, 1484, 1453, 1358, 1305, 1147.

[α]_(D)=+13.0° (CH₃OH, c=1.02, 24° C.),

mp. 160-161° C.

No. 1a-177

CDCl₃ 300 MHz

0.96-1.88(14H, m), 1.88-2.26(3H, m), 2.94(1H, m), 3.67(3H, s), 3.87(3H, s), 4.67(1H, brs), 5.08-5.14(2H, m), 6.77(1H, d, J=1.5 Hz), 6.99-7.02(2H, m), 7.53-7.57(1H, m), 7.65-7.70(3H, m), 8.00(1H, s), 9.27(1H, brs).

IR(CHCl₃): 3426, 3376, 3006, 2952, 1724, 1610, 1495, 1438, 1357, 1308, 1282, 1249, 1177, 1147/cm.

[α]_(D)=+18.1° (CHCl₃, c=1.02, 22° C.).

No. 1a-178

CDCl₃+CD₃OD 300 MHz

0.96-1.91(14H, m), 2.19(1H, m), 2.27(2H, t, J=6.0 Hz), 2.85(1H, m), 3.87(3H, s), 5.16-5.23(2H, m), 6.99-7.02(2H, m), 7.41(1H, m), 7.64-7.73(3H, m), 7.92(1H, m).

IR(CHCl₃): 3366, 3261, 3004, 2954, 2873, 1705, 1611, 1496, 1458, 1438, 1304, 1286, 1253, 1180, 1149, 1128/cm.

[α]_(D)=+14.6° (CHCl₃, c=1.02, 22° C.).

No. 1a-179

CDCl₃+CD₃OD 300 MHz

0.96-1.87(14H, m), 2.15-2.23(3H, m), 2.93(1H, m), 3.85(3H, s), 5.10-5.16(2H, m), 6.90-6.93(2H, m), 7.50(1H, m), 7.60-7.65(3H, m), 7.91(1H, d, J=0.9 Hz).

IR(CHCl₃): 3369, 3270, 2950, 2873, 1719, 1612, 1498, 1456, 1440, 1359, 1306, 1269, 1219, 1146, 1127/cm.

[α]_(D)=+18.1° (CH₃OH, c=1.00, 22° C.).

No. 1a-180

CDCl₃+CD₃OD 300 MHz

1.03-1.86(14H, m), 2.08-2.17(3H, m), 2.91(1H, m), 5.06-5.10(2H, m), 6.76(1H, m) 6.86-6.90(2H, m), 7.48(1H, m), 7.61-7.69(3H, m), 7.89(1H, m).

IR(CHCl₃): 3360, 3259, 2954, 2873, 1706, 1612, 1497, 1457, 1360, 1306, 1272, 1230, 1176, 1148, 1126/cm.

[α]_(D)=+20.3° (CH₃OH, c=1.00, 22° C.).

No. 1a- 181

CDCl₃300 MHz

0.97-1.96(14H, m), 2.15(1H, m), 2.29(2H, t, J=6.9 Hz), 3.05(1H, m), 3.81(3H, s), 5.08(1H, d, J=6.9 Hz), 5.23-5.25(2H, m), 6.62(1H, s), 7.47-7.54(5H,m), 7.59(1H, m), 7.70(1H, m), 7.97(1H, m).

IR(CHCl₃): 3380, 3260, 3020, 2946, 2868, 1708, 1466, 1388, 1328, 1149/cm.

[α]_(D)=+32.9° (CHCl₃, c=1.07, 22° C.).

No. 1a- 182

CDCl₃300 MHz

0.94-1.90(14H, m), 2.25(2H, t, J=7.5 Hz), 2.30(1H, m), 2.98(1H, m), 3.70(3H, s), 4.83(1H, d, J=6.6 Hz), 5.13-5.16(2H, m), 6.95(1H, d, J=1.5 Hz), 7.11-7.23(2H, m), 7.43(1H, d, J=8.1 Hz), 7.65(1H, d, J=81 Hz), 7.79-7.93(4H, m), 9.08(1H, br).

IR(CHCl₃): 3458, 3372, 3020, 3002, 2946, 2868, 1719, 1598, 1452, 1422, 1321, 1300, 1157/cm.

[α]_(D)=6.6° (CHCl₃, c=1.00), mp 150-151° C.

No. 1a-183

CDCl₃300 MHz

0.95-1.94(14H, m), 2.26(1H, m), 2.28(2H, t, J=7.5 Hz), 3.00(1H, m), 5.16-5.19(2H, m), 5.32(1H, d, J=7.2 Hz), 6.93(1H, d, J=1.2 Hz), 7.13(1H, m), 7.22(1H, dd, J=7.8, 6.6 Hz), 7.42(1H, d, J=7.8 Hz), 7.63(1H, d, J=7.8 Hz), 7.76(2H, d, J=8.4 Hz), 7.90(2H, d, J=8.4 Hz), 8.95(1H, br).

IR(CHCl₃): 3458, 3374, 3260, 3020, 3002, 2948, 2868, 1708, 1598, 1452, 1422, 1301, 1156/cm.

[α]_(D)=+17.9° (CHCl₃, c=1.01, 22° C.).

No. 1a- 184

CDCl₃200 MHz

0.92-2.00(14H, m), 2.20(1H, m), 2.34(2H, t, J=6.8 Hz), 3.05(1H, m), 5.20-5.36(3H, m), 7.39-7.44(2H, m), 7.61-7.66(1H, m), 7.80-7.84(1H, m), 8.05(2H, d, J=8.6 Hz), 8.40(2H, d, J=8.6 Hz).

IR(CHCl₃): 3384, 3271, 3019, 2958, 1709, 1615, 1599, 1551, 1453, 1405, 1344, 1326, 1243, 1163/cm.

[α]_(D)=+18.5° (CHCl₃, c=1.00, 21° C.).

No. 1a- 185

CDCl₃300 MHz

0.89-2.20(15H, m), 2.26(2H, d.t, J=2.1 and 7.2 Hz), 2.99(1H, m), 5.08(1H, d, J=6.3 Hz), 5.09-5.24(2H, m), 6.90(1H, d, J=1.2 Hz), 7.32-7.48(4H, m), 7.64-7.72(3H, m), 8.20(1H, d, J=1.2 Hz), 9.00(1H, s).

IR(CHCl₃): 3464, 3375, 3275, 3022, 2956, 1707, 1605, 1490, 1449, 1356, 1322, 1219, 1147, 1131/cm.

[α]_(D)=+21.6° (CHCl₃, c=1.01, 23° C.).

No. 1a- 186

CDCl₃: 300 MHz

1.36-2.24(14H, m), 2.31(2H, t, J=7.4 Hz), 2.49(1H, brs), 3.37(1H, m), 3.67(3H,m s), 5.38-5.50(2H, m), 7.40-7.68(9H, m).

IR(CHCl₃): 3375, 1727, 1602, 1435, 1362, 1221, 1207, 1168, 1045/cm.

No. 1a- 187

CDCl₃: 300 MHz

1.10-2.25(14H, m), 2.36(2H, t, J=7.2 Hz), 2.47(1H, m), 3.37(1H, m), 5.35-5.54(2H, m), 5.62(1H, d, J=7.2 Hz), 7.39-7.70(9H, m).

IR(CHCl₃): 3674, 3496, 3376, 3234 , 3012 , 2952 , 2880 , 2650 , 1725(sh), 1709, 1602, 1485 , 1420, 1360, 1167/cm.

[α]_(D)=+32° (CHCl₃, c=1.69).

No. 1a- 188

CDCl₃200 MHz

0.86-1.92(14H, m), 2.22(3H, m), 2.36(3H, s), 2.95(1H, m), 3.67(3H, s), 3.93(3H, s), 4.81(1H, d, J=6.2 Hz), 5.04-5.20(2H, m), 7.02-7.05(2H, m), 7.31(1H, d, J=8.6 Hz), 7.39(1H, d, J=7.8 Hz), 7.79-7.89(3H, m).

IR(CHCl₃): 3385, 3286, 3029, 3019, 3015, 2954, 2877, 1718, 1617, 1598, 1567, 1507, 1311, 1269, 1153/cm.

[α]_(D)=−29.4° (CHCl₃, c=1.01, 25° C.).

No. 1a-189

[α]_(D)=−7.7° (CHCl₃, c=1.00, 24° C.).

No. 1a-190

[α]_(D)=−17.3° (CHCl₃, c=1.00, 24° C.).

No. 1a-191

CDCl₃300 MHz

0.95-2.20(14H, m), 2.30(1H, m), 2.36(2H, d, J=6.9 Hz), 3.21(1H, m), 4.25(2H, s), 7(1H, d, J=7.8 Hz), 5.35-5.48(2H, m), 7.25(1H, dd, J=1.8 and 8.1 Hz), 7.32-7.35(2H, m), 7.59(1H, d, J=8.1 Hz), 7.94(1H,s), 8.14(1H, d, J=2.7 Hz), 8.23(1H, d.d, J=2.7 and 8.7 Hz).

IR(CHCl₃): 3386, 3026, 3015, 2957, 2877, 2633, 1702, 1617, 1573, 1530, 1348, 1123/cm.

[α]_(D)=−6.1° (CHCl₃, c=1.01, 25° C.).

No. 1a-192

CDCl₃300 MHz

0.92-2.20(14H, m), 2.13(3H, m), 3.23(1H, m), 3.64(3H, s), 3.94(3H, s), 4.22(2H, s), 4.36(1H, d, J=7.8 Hz), 5.37-5.42(2H, m), 7.16-7.42(6H, m), 7.53(1H, d, J=8.4 Hz), 7.94(1H, s).

IR(CHCl₃): 3389, 3022, 3013, 2953, 2877, 1716, 1616, 1560, 1485, 1340, 1326, 11245/cm.

[α]_(D)=−15.2° (CHCl₃, c=1.01, 25° C.).

No. 1a -193

CDCl₃300 MHz

0.92-2.20(14H, m), 2.25(1H, m), 2.35(2H, t, J=7.2 Hz), 3.17(1H, m), 4.22(2H, s), 4.91(1H, d, J=7.5 Hz), 5.37-5.42(2H, m), 7.13-7.43(6H, m), 7.60(1H, d, J=8.1 Hz), 8.05(1H, s).

IR(CHCl₃): 3511, 3387, 3029, 3020, 3011, 2957, 2877, 2651, 1698, 1614, 1560, 1505, 1320, 1280, 1252, 1126/cm.

[α]_(D)=−0.9° (CHCl₃, c=1.00, 25° C.).

No. 1a-1

CDCl₃300 MHz

0.98-1.56(15H, m), 1.85-1.90(5H, m), 2.23(1H, m), 3.05(1H, m), 3.66(3H, s), 4.77(1H, d, J=6.0 Hz), 5.08-5.28(2H, m), 7.46(3H, m), 7.38-7.54(2H, d, J=7.5 Hz), 7.72(2H, d, J=8.4 Hz), 7.93(2H, d, J=8.4 Hz).

IR(CHCl₃): 3384, 3028, 2952, 2876, 1719, 1595, 1391, 1322, 1155/cm.

[α]₄₃₆+4.0˜+6.0(CHCl₃, c=1.00, 23° C.).

mp. 96-98° C.

No. 1b-2

CDCl₃ 300 MHz

0.98-1.52(15H, m), 1.85-1.90(5H, m), 2.17(1H, m), 3.00(1H, m), 3.67(3H, s), 4.05(2H, s), 4.83(1H, d, J=6.0 Hz), 5.05-5.23(2H, m), 7.14(2H, d, J=7.2 Hz), 7.17-7.32(5H, m), 7.78(2H, d, J=8.4 Hz).

IR(CHCl₃): 3384, 3026, 2952, 2874, 1719, 1595, 1453, 1407, 1320, 1180/cm.

[α]_(D)=+2.5° (CHCl₃, c=1.02, 24° C.).

No. 1b-3

CDCl₃ 300 MHz

0.96-2.05(20H, m), 2.07(1H, m), 3.07(1H, m), 4.04(2H, s), 5.21-5.35(2H, m), 5.55(1H, d, J=6.9 Hz), 7.14(2H, d, J=6.6 Hz), 7.20-7.32(5H, m), 7.78(2H, d, J=8.1H).

IR(CHCl₃): 3250, 3022, 2950, 1699, 1596, 1495, 1453, 1405, 1318, 1153/cm.

[α]_(D)=+17.1° (CHCl₃, c=1.01, 25° C.).

mp. 129-131° C.

No. 1b-4

CDCl₃ 200 MHz

0.90-2.10(15H, m), 1.19(3H, s), 1.20(3H, s), 3.11(1H, m), 5.24-5.32(2H, m), 5.70(1H, d, J=6.6 Hz), 7.38-7.68(4H, m), 7.96-8.04(2H, m), 8.53(1H, d, J=1.4 Hz).

IR(CHCl₃): 3384, 3246, 2958, 1701, 1632, 1595, 1468, 1445, 1322, 1216, 1202, 1190, 1155, 1122/cm.

[α]_(D)=+10.8° (CHCl₃, c=0.51, 23° C.).

No. 1b-5

1.02-2.10(15H, m), 1.16(6H, s), 3.02(1H, m), 4.09(3H, s), 5.23-5.28(2H, m), 5.76(1H, d, J=7.2 Hz), 7.36-7.63(4H, m), 7.97(1H, d, J=7.8 Hz), 8.16(1H, s).

IR(CHCl₃): 3369, 2959, 1702, 1635, 1585, 1468, 1454, 1441, 1415, 1318, 1222, 1189, 1170, 1154/cm.

[α]_(D)=+9.9° (CHCl₃, c=1.00, 23° C.).

No. 1c-1

CDCl₃ 300 MHz

1.10-2.02(14H, m), 2.27(2H, t, J=7.5 Hz), 2.50(1H, m), 2.89(3H, s), 3.31(1H, m), 3.64(3H, s), 5.16-5.30(2H, m), 7.34-7.42(3H, m), 7.50-7.59(2H, m), 7.62-7.68(2H, m), 7.76-7.82(2H, m).

IR(CHCl₃): 3020, 2946, 2868, 2212, 1727, 1596, 1495, 1437, 1339, 1156, 1135, 1084/cm.

[α]_(D)=−16.1° (CHCl₃, c=1.05, 25.0° C.).

m.p. 100-102° C.

No. 1c-2

CDCl₃ 300 MHz

1.10-2.05(14H, m), 2.23(2H, t, J=7.5 Hz), 2.53(1H, m), 2.91(3H, s), 3.35(1H, m), 3.62(3H, s), 5.02-5.30(2H, m), 7.50-7.60(3H, m), 7.90-8.08(6H, m).

IR(CHCl₃): 3016, 2946, 2868, 1728, 1437, 1398, 1340, 1160, 1086/cm.

[α]_(D)=−32.5° (CHCl₃, c=1.00, 25.0° C.).

No. 1c-3

CD₃OD 300 MHz

1.15-2.05(14H, m), 2.13(2H, t, J=7.2 Hz), 2.47(1H, m), 2.91(3H, s), 3.27(1H, m), 4.90-5.30(2H, m), 7.37-7.44(3H, m), 7.53-7.61(2H, m), 7.71-7.77(2H, m), 7.81-7.87(2H, m).

IR(KBr): 3412, 2999, 2951, 2871, 2217, 1560, 1399, 1243, 1159, 1137, 1103, 1084.

[α]_(D)=−8.6° (CH₃OH, c=1.03, 23° C.).

No. 1d-1

CDCl₃ 300 MHz

1.00-2.16(15H, m), 2.36(2H, t, J=7.2 Hz), 3.17(1H, m), 3.33(3H, s), 5.23-5.43(3H, m), 7.51-7.59(3H, m), 7.91-8.10(6H, m), 9.02(1H, brs).

IR(CHCl₃): 3382, 3268, 3028, 2954, 2874, 1715, 1442, 1400, 1337, 1162, 1120, 1089/cm.

[α]_(D)=+40.0° (CHCl₃, c=0.53, 22° C.).

No. 1d-2

CDCl₃ 300 MHz

1.03-2.30(17H, m), 3.03(1H, m), 4.03(2H, s), 5.26(2H, m), 5.84(1H, br), 5.25-5.29(1H, d, J=6.6 Hz), 6.03(1H, br), 7.14(2H, d, J=8.1 Hz), 7.26-7.31(5H, m), 7.80(2H, d, J=8.1 Hz).

IR(CHCl₃): 3376, 3002, 2946, 1669, 1595, 1492, 1454, 1406, 1318, 1154/cm.

[α]_(D)=+^(4.3)° (CHCl₃, c=1.00, 23° C.).

No. 1d-3

CDCl₃ 300 MHz

0.96-2.17(17H, m), 2.33(2H, t, J=6.9 Hz), 3.01(1H, m), 4.04(2H, s), 5.10(1H, d, J=6.6 Hz), 5.21-5.26(2H, m), 7.14(2H, d, J=8.7 Hz), 7.16-7.32(5H, m), 7.78(2H, d, J=8.4 Hz).

IR(CHCl₃): 3260, 3020, 2946, 1711, 1596, 1492, 1457, 1407, 1318, 1154/cm.

[α]_(D)=+9.3° (CHCl₃, c=1.09, 25° C.).

No. 1d-4

CDCl₃ 300 MHz

0.95-2.14(15H, m), 2.34(2H, t, J=7.2 Hz), 3.09(1H, m), 3.30(3H, s), 4.04(2H, s), 5.19(1H, d, J=7.2 Hz), 5.22-5.39(2H, m), 7.10-7.35(7H, m), 7.81(2H, d, J=8.1 Hz), 9.10(1H, brs).

IR(CHCl₃): 3382, 3260, 3028, 2952, 2874, 2670, 1713, 1595, 1492, 1450, 1405, 1338, 1160, 1120, 1092/cm.

[α]_(D)=+22.2° (CHCl₃, c=1.07, 22° C.).

No. 1d-5

CDCl₃ 300 MHz

1.00-2.10(14H, m), 2.30-2.39(3H, m), 3.15(1H, m), 3.35(3H, s), 5.18-5.40(3H, m), 7.41(1H, d.t., J=0.9 and 7.8 Hz), 7.50-7.69(3H, m), 7.88-8.15(2H, m), 8.60(1H, d, J=1.5 Hz), 9.06(1H, s).

IR(CHCl₃): 3382, 3268, 3028, 2954, 2874, 1714, 1442, 1402, 1338, 1188, 1155, 1121, 1072/cm.

[α]_(D)=+15.3° (CHCl₃, c=1.00, 22° C.).

No. 1e-1

CDCl₃ 300 MHz

1.19-2.45(19H, m), 2.58(1H, m), 5.63(1H, d, J=3.0 Hz), 7.42-7.65(4H, m), 7.94-8.03(2H, m), 8.49-8.50(1H, m).

IR(CHCl₃): 3293, 3024, 1710, 1595, 1584, 1467, 1445, 1410, 1324, 1222, 1213, 1206, 1190, 1160/cm.

[α]_(D)=−41.1° (CHCl₃, c=1.01, 23° C.).

No. 1e-2

CDCl₃ 300 MHz

1.10-2.25(19H, m), 2.94(1H, m), 4.12(3H, s), 5.53(1H, d, J=7.2 Hz), 7.39(1H, m), 7.50-762(3H, m), 7.96(1H, d, J=7.5 Hz), 8.13(1H, s).

IR(CHCl₃): 3367, 3025, 2955, 1711, 1634, 1600, 1584, 1468, 1454, 1440, 1415, 1342, 1317, 1222, 1189, 1157/cm.

[α]_(D)=+1.2° (CHCl₃, c=1.00, 25° C.).

No. 1f-1

CDCl₃ 300 MHz

1.08-2.47(19H, m), 2.56(1H, m), 3.52(2H, t, J=6.6 Hz), 5.59(1H, d, J=2.4 Hz), 7.40-7.66(4H, m), 7.95-8.04(2H, m), 8.50(1H, d, J=1.8 Hz).

IR(CHCl₃): 3624, 3383, 3295, 2950, 2877, 1705, 1595, 1584, 1468, 1445, 1405, 1347, 1337, 1324, 1224, 1190, 1160/cm.

[α]_(D)=−54.1° (CHCl3, c=1.01, 23° C.).

No. 1f-2

CDCl₃ 300 MHz

1.08-2.24(19H, m), 2.94(1H, m), 3.53(2H, t, J=6.3 Hz), 4.13(3H, s), 5.47(1H, d, J=6.6 Hz), 7.36-7.63(4H, m), 7.96(1H, d, J=6.3 Hz), 8.14(1H, s).

IR(CHCl₃): 3625, 3368, 3025, 3013, 2949, 2877, 1710, 1634, 1600, 1584, 1468, 1454, 1440, 1415, 1342, 1317, 1232, 1220, 1189, 1157/cm.

[α]_(D)=−5.6° (CHCl₃, c=1.00, 25° C.).

No. 1g-1

CDCl₃ 200 MHz

1.17-2.34(15H, m), 3.22(1H, m), 5.10-5.16(2H, m), 5.45(1H, d, J=7.0 Hz), 7.35-7.66(4H, m), 7.95-8.01(2H, m), 8.51(1H, d, J=2.0 Hz).

IR(CHCl₃): 3383, 3275, 2959, 1707, 1595, 1584, 1468, 1445, 1425, 1319, 1269, 1248, 1190, 1149, 1123/cm.

[α]_(D)=+64.3° (CHCl₃, c=1.01, 23° C.).

No. 1g-2

CDCl₃ 300 MHz

1.10-2.15(13H, m), 2.36(2H, t, J=7.2 Hz), 3.21(1H, m), 4.09(3H, s), 5.10-5.22(2H, m), 5.43(1H, d, J=7.8 Hz), 7.36-7.62(4H, m), 7.96(1H, d,J=7.8 Hz), 8.12(1H, s).

IR(CHCl₃): 3366, 2959, 1708, 1635, 1600, 1585, 1467, 1454, 1440, 1415, 1345, 1318, 1233, 1189, 1152/cm.

[α]_(D)=+103.1° (CHCl₃, c=1.01, 23° C.).

No. 1h-1

CDCl₃ 300 MHz

0.90-1.60(17H, m), 1.83(1H, m), 2.11(1H,m), 2.22(2H, t, J=7.2 Hz), 3.07(1H, m), 5.11(1H, d, J=7.2 Hz), 7.38-7.47(1H, m), 7.50-7.60(1H, m), 7.60-7.72(2H, m), 7.88-8.12(2H, m), 8.54(1H, d, J=0.9 Hz).

IR(CHCl₃): 3382, 3274, 2926, 1707, 1464, 1442, 1318, 1266, 1188, 1153, 1121, 1105, 1071, 1019/cm.

[α]_(D)=−2.8° (CHCl₃, c=1.01, 23° C.).

No. 1i-1

[α]₃₅₅ +50.9° (CHCl₃, c=1.01, 24° C.).

No. 1i-2

CDCl₃ 300 MHz

0.98-1.70(1 1H, m), 1.80-2.00(5H, m), 2.19(1H, m), 3.03(1H, m), 3.64(2H, t, J=6.6 Hz), 4.05(2H, s), 4.69(1H, d, J=6.6 Hz), 5.15(1H, m), 5.25(1H,m), 7.16(2H, d, J=7.2 Hz), 7.27-7.32(5H, m), 7.77(2H, d, J=8.4 Hz).

IR(CHCl₃): 3376, 3004, 2946, 2316, 1596, 1492, 1453, 1407, 1318, 1154/cm.

[α]_(D)=+3.5° (CHCl₃, c=1.00, 22° C.).

mp. 80.5-82.0° C.

No. 1j-1

[α]₄₃₆=−7.5+0.5° (CHCl₃, c=1.05, 22° C.).

No. 1j-2

[α]_(D)=−9.7+0.5° (CHCl₃, c=1.06, 22° C.).

No. 1j-3

[α]_(D)=+15+0.5° (CH₃OH, c=1.06, 24.5° C.).

mp. 101-108° C.

No. 1j-4

[α]_(D)=−28.0±0.6° (CHCl₃, c=1.06, 24° C.).

mp. 159-161° C.

1j-5

[α]_(D)=−12.5±0.5° (CHCl₃, c=1.04, 23° C.).

mp. 99-101° C.

No. 1j-6

CDCl₃ 300 MHz

0.90-2.03(14H, m), 2.20(1H, m), 2.30(2H, t, J=7.3 Hz), 3.00(1H, m) 3.68(3H, s), 4.76(1H, d, J=6.8 Hz), 5.13-5.35(2H, m), 7.01-7.08(4H, m), 7.19-7.26(1H, m), 7.37-7.46(2H, m), 7.80-7.84(2H, m).

IR(CHCl₃): 3382, 3280, 3080, 3016, 2952, 2900, 1727, 1582, 1486, 1432, 1322, 1150/cm.

[α]_(D)=−31.0° (CHCl₃, c=1.05, 26° C.).

No. 1j-7

CDCl₃ 300 MHz

0.91-2.09(14H, m), 2.15(1H, m), 2.35(2H, t, J=7.5 Hz), 3.01(1H, m), 5.17(1H, d, J=6.8 Hz), 5.21-5.34(2H, m), 7.01-7.08(4H, m), 7.15-7.27(1H, m), 7.37-7.43(2H, m), 7.8-7.85(2H, m).

IR(CHCl₃): 3474, 3386, 3270, 3024, 2958, 2900, 2675, 1711, 1584, 1488, 1420, 1323, 1298, 1150/cm.

[α]_(D)=−13.4° (CHCl₃, c=1.01, 26° C.).

No. 1j-8

CDCl₃ 300 MHz

0.95-2.14(13H, m), 2.30(2H, t, J=7.5 Hz), 2.36(1H, m), 2.84(1H, m), 2.9(1J=4.8 Hz), 3.66(3H, s), 5.33-6.52(2H, m), 6.82-6.87(1H, m), 6.93-7.00(2H, m), 7.09-7.155(4H, m), 7.28-7.36(2H, m), 7.54-7.59(1H, m).

IR(CHCl₃): 3350, 3010, 2950, 2880, 1728, 1603, 1582, 1489 1461, 1438, 1360, 1160/cm.

[α]_(D)=+75.1° (CHCl₃, c=1.13, 26° C.).

No. 1j-9

CDCl₃ 300 MHz

0.95-2.03(14H, m), 2.20(1H, m), 2.29(2H, t, J=7.5 Hz), 3.06(1H, m), 3.68(3H, s), 4.98(1H, d, J=7.4 Hz), 5.14-5.34(2H, m), 7.46-7.54(2H, m), 7.60-7.68(1H, m), 7.75-7.80(2H, m), 7.88-7.92(2H, m), 7.99-8.03(2H, m).

IR(CHCl₃): 3384, 3280, 3020, 2960, 2888, 1727, 1662, 1600, 1316, 1273, 1163/cm.

[α]_(D)=−41.0° (CHCl₃, c=1.17, 26° C.).

No. 1j-10

CDCl₃+CD₃OD 300 MHz

0.94-2.08(14H, m), 2.21(1H, m), 2.34(2H, t, J=6.2 Hz), 3.04(1H, m), 5.21-5.35(2H, m), 5.40(1H, m), 7.49-7.58(2H, m), 7.64-7.68(1H, m), 7.79-8.06(6H, m).

IR(CHCl₃): 3475, 3370, 3250, 3018, 2956, 2976, 2650, 1709, 1662, 1595, 1445, 1420, 1395, 1317, 1274, 1163/cm.

[α]_(D)=−17.1° (CHCl₃, c=1.13, 25° C.).

No. 1j-11

CDCl₃ 300 MHz

1.06-1.98(14H, m), 2.24-2.29(3H, m), 3.13(1H, m), 3.66(3H, s), 5.10-5.24(2H, m), 5.40(1H, d, J=6.3 Hz), 7.39-7.49(3H, m), 7.59-7.64(3H, m), 7.80-7.83(2H, m), 8.08-8.11 (1H, m).

IR(CHCl₃): 3302, 3012, 2948, 2905, 1727, 1661, 1593, 1435, 1332, 1312, 1287, 1271, 1165/cm.

[α]_(D)=+15.6° (CHCl₃, c=1.03, 26° C.).

No. 1j-12

CDCl₃ 300 MHz 1.08-1.98(14H, m), 2.23(1H, m), 2.33(2H, t, J=7.5 Hz), 3.16(1H, m), 5.18-5.26 (2H, m), 5.39-5.45(1H, m), 7.39-7.49(3H, m), 7.60-7.64(3H, m), 7.80-7.83(2H, m), 8.09-8.12(1H, m).

IR(CHCl₃): 3325, 3022, 2956, 2872, 2680, 1708, 1662, 1603, 1598, 1425, 1340, 1316, 1288, 1271, 1165/cm.

[α]_(D)=+9.7° (CHCl₃, c=0.52, 25° C.).

No. 1j-13

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.2 0(1H, m), 2.27(2H, t,J=6.3 Hz), 3.03(1H, m), 3.67(3H, s), 4.99(1H, d, J=6.6 Hz), 5.12 -5.31(2H, m), 7.47-7.55(2H, m), 7.60-7.69(2H, m) 7.76-7.81(2H, m), 7.96-8.05(1H, m), 8.08-8.14(1H, m), 8.27-8.28(1H, m).

IR(CHCl₃): 3674, 3538, 3376, 3276, 3012, 2948, 2860, 1726, 1662, 1595, 1440, 1335, 1317, 1297, 1274, 1166, 1150/cm.

[α]_(D)=+10.2° (CHCl₃, c=1.00, 25° C.).

No. 1j-14

CDCl₃ 300 MHz

0.93-2.08(14H, m), 2.21(1H, m), 2.32(2H, t, J=6.3 Hz), 3.00(1H,m), 5.20-5.36(2H, m), 5.38(1H, d, J=6.2 Hz), 7.50-7.55(2H, m), 7.63-7.71(2H, m), 7.77-7.81(2H, m), 7.99-8.04(1H, m), 8.10-8.18(1H, m), 8.32-8.36(1H, m).

IR(CHCl₃): 3674, 3480, 3374, 3258, 3012, 2950, 2875, 2650, 1709, 1662, 1598, 1418, 1335, 1317, 1274, 1143/cm.

[α]_(D)=+61.0° (CHCl₃, c=1.19, 25° C.).

No. 1j-15

CDCl₃ 300 MHz

0.90-2.00(14H, m), 2.19(1H, m), 2.30(2H, t, J=7.3 Hz), 3.01(1H, m), 3.67(3H, s), 4.82(1H, d, J=6.6 Hz), 5.14-5.34(2H, m), 7.36-7.39(3H, m), 7.53-7.57(2H, m), 7.62-7.6(2H, m), 7.83-7.88(2H, m).

IR(CHCl₃): 3376, 3276, 3010, 2948, 2868, 2212, 1727, 1597, 1500, 1437, 1325, 1161/cm.

[α]_(D)=−7.2° (CHCl₃, c=1.00, 26° C.).

No. 1j-16

CDCl₃ 300 MHz

0.93-2.03(14H, m), 2.15(1H, m), 2.36(2H, t, J=7.5 Hz), 3.05(1H, m), 5.20-5.40(3H, m), 7.36-7.39(3H, m), 7.55-7.66(4H, m), 7.84-7.88(2H, m).

IR(CHCl₃): 3470, 3376, 3260, 3012, 2950, 2868, 2675, 2212, 1708, 1596, 1503, 1416, 1396, 1322, 1160.

[α]_(D)=−22.4° (CHCl₃, c=1.00, 26° C.).

No. 1j-17

CDCl₃ 300 MHz 1.00-1.60(9H, m), 1.79-1.89(5H, m), 2.17(1H, brs), 2.23(2H, t, J=7.2 Hz), 3.03(1H, m), 5.10-5.23(2H, m), 5.49(1H, d, J=6.6 Hz), 7.40(1H, t, J=7.4 Hz), 7.53(1H, t, J=7.2 Hz), 7.60-7.68(2H, m), 7.98-8.03(2H, m), 8.55(1H, d, J=1.5 Hz).

IR(CHCl₃): 3516, 3384, 3270, 2666, 1708, 1632, 1595, 1584, 1467, 1445, 1425, 1374, 1345, 1321, 1269, 1248, 1218/cm.

[α]_(D)=−7.8° (CHCl₃, c=1.01, 22° C.).

No. 1j-18

CDCl₃ 300 MHz

0.90-2.03(14H, m), 2.19(1H, m), 2.30(2H, t, J=7.5 Hz), 3.00(1H, m), 3.67(3H, s), 4.80(1H, d, J=6.4 Hz), 5.14-5.35(2H, m), 6.99-7.04(2H, m), 7.16-7.22(2H, m), 7.34-7.49(4H, m), 7.57-7.61(1H, m).

IR(CHCl₃): 3376, 3276, 3012, 2948, 2875, 1727, 1583, 1488, 1471, 1432, 1330, 1311, 1150/cm.

[α]_(D)=+54.0° (CHCl₃, c=0.99, 25° C.).

No. 1j-19

CDCl₃ 300 MHz

0.91-2.09(14H, m), 2.15(1H, m), 2.34(2H, t, J=7.5 Hz), 3.01(1H, m), 5.16(1H, d, J=6.6 Hz), 5.24-5.40(2H, m), 7.01-7.08(2H, m), 7.15-7.25(2H, m), 7.35-7.53(4H, m), 7.59-7.65(1H, m).

IR(CHCl₃): 3470, 3376, 3260, 3012, 2950, 2875, 2640, 1708, 1583, 1488, 1471, 1430, 1335, 1305, 1149/cm.

[α]_(D)=−21.0° (CHCl₃, c=1.30, 25° C.).

No. 1j-20

CDCl₃ 300 MHz 1.17(1H, m), 1.26-1.34(2H, m), 1.54-2.24(11H, m), 2.31(2H, t, J=7.4 Hz), 2.48(1H, brs), 3.37(1H, m), 3.67(3H, s), 5.35-5.50(2H, m), 7.39-7.68(9H, m).

IR(CHCl₃): 3377, 1727, 1601, 1435, 1362, 1168/cm.

No. 1j-21

CDCl₃ 300 MHz

1.10-2.25(14H, m), 2.36(2H, t, J=7.2 Hz), 2.47(1H, m), 2.89(1H, m), 5.35-5.53(2H, m), 5.63(1H, d, J=7.2 Hz), 7.40-7.71(9H, m).

IR(CHCl₃): 3674, 3496, 3374, 3234, 3010, 2952, 2870, 2640, 1730(sh), 1710, 1605, 1485, 1425, 1360, 1167/cm.

[α]_(D)=−43.0° (CHCl₃, c=1.01, 25° C.).

No. 1j-22

CDCl₃ 300 MHz

0.98-1.95(14H, m), 2.25-2.31(3H, m), 2.95(1H, m), 5.19-5.30(2H, m), 5.33(1H, d, J=3.9 Hz), 6.58(1H, d, J=7.5 Hz), 6.80(1H, t, J=7.5 Hz), 6.99-7.05(1H, m), 7.44-7.53(6H, m), 7.60-7.73(9H, m), 7.94-7.73(3H, m), 8.23-8.26(2H, m), 10.66(1H, s).

IR(CHCl₃): 3475, 3372, 3260, 3008, 2952, 2868, 2722, 1725, 1710(sh), 1663, 1590, 1571, 1525, 1448, 1437, 1345, 1314, 1161, 112/cm.

[α]_(D)=+12.90° (CHCl₃, c=0.12, 23° C.).

No. 1j-23

CDCl₃ 300 MHz 0.94˜1.94(14H, m), 2.23-2.30(3H, m), 2.98(1H, m), 3.68(3H, s), 5.09(1H, d, J=6.2 Hz), 5.15-5.28(2H, m), 7.14-7.22(1H, m), 7.34-7.42(2H, m), 7.68-7.73(2H, m), 7.89-8.03(4H, m), 8.51(1H, s).

IR(CHCl₃): 3372, 3275, 1724, 1673, 1599, 1438, 1320, 1161/cm.

[α]_(D)=+17.0° (CHCl₃, c=1.38, 25° C.).

No. 1j-24

CDCl₃+CD₃OD 300 MHz

0.96-2.05(14H, m), 2,25-2.34(3H, m), 2.92(1H, m), 5.16-5.34(2H, m), 7.14-7.22(1H, m), 7.29-7.42(2H, m), 7.70(2H, d, J=7.6 Hz), 7.92-8.05(4H, m).

IR(CHCl₃): 3616, 3426, 3375, 3010, 2950, 2828, 2645, 1708, 1672, 1599, 1439, 1323, 1161/cm.

[α]_(D)=+21.0° (CH₃OH, c=1.00, 22° C.).

No. 1j-25

CDCl₃ 300 MHz

1.03(1H, m), 1.18-2.01(13H, m), 2.20(1H, brs), 2.27(2H, t, J=7.4 Hz), 3.08(1H, m), 3.66(3H, s), 5.11(1H, d, J=6.6 Hz), 5.14-5.34(2H, m), 7.54-7.62(3H, m), 8.04-8.32(6H, m).

IR(CHCl₃): 3384, 3278, 1726, 1605, 1484, 1448, 1331, 1161/cm.

No. 1j-26

CDCl₃+CD₃OD 300 MHz

1.03-2.10(14H, m), 2.22(1H, m), 2.31(2H, t, J=7.5 Hz), 2.98(1H, m), 5.23-5.38(2H, m), 7.55-7.66(3H, m), 8.05-8.08(2H, m), 8.14-8.18(2H, m), 8.28-8.31(2H, m).

IR(Nujol): 3260, 2720, 2660, 1711, 1545, 1460, 1317, 1163/cm.

[α]_(D)=+15.80° (CH₃OH, c=1.01, 22° C.).

No. 1j-27

[α]_(D)=+16.7° (CHCl₃, c=1.00, 23° C.).

No. 1j-28

CDCl₃ 300 MHz

1.01(1H, m), 1.14-1.29(2H, m), 1.46-2.19(11H, m), 2.33(2H, t, J=7.2 Hz), 2.41(1H, brs), 3.18-3.21(5H, m), 3.68(3H, s), 3.73-3.76(4H, m), 4.37(1H, d, J=7.2 Hz), 5.35-5.45(2H, m).

IR(CHCl₃): 3392, 1727, 1435, 1335, 1148/cm.

[α]_(D)=+10.7° (CHCl₃, c=1.39, 26° C.).

No. 1j-29

CDCl₃ 300 MHz

1.00(1H, m), 1.20-1.29(2H, m), 1, 48-2.25(12H, m),2.37(2H, t, J=7.2 Hz), ,3.17-3.22(5H, m), 3.74-3.79(4H, m), 4.79(1H, d, J=7.8 Hz), 5.34-5.54(2H, m).

IR(CHCl₃): 3470, 3390, 3270, 2675, 1709, 1455, 1420, 1315, 1147/cm.

[α]_(D)=+16.8° (CHCl₃, c=1.42, 26° C.).

No. 1k-1

[α]_(D)=−25.4° (CHCl₃, c=1.08, 23° C.).

No. 1k-2

CDCl₃ 200 MHz

1.07-2.28(14H, m), 2.32(2H, t, J=7.4 Hz), 2.63(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.52(2H, m), 6.35(1H, d, J=7.0 Hz), 7.48-7.60(3H, m), 7.88-8.02(6H, m).

IR(CHCl₃): 3438, 3002, 2946, 2868, 1727, 1652, 1514, 1485, 1363, 1310, 1245, 1154/cm.

[α]_(D)=−80.4° (CHCl₃, c=1.01, 24.0° C.).

No. 1k-3

CDCl₃ 200 MHz

1.10-2.26(14H, m), 2.37(2H, t, J=7.2 Hz), 2.60(1H, m), 3.93(1H, m), 5.30-5.50(2H, m), 6.33(1H, d, J=7.5 Hz), 7.48-7.58(3H, m), 7.88-7.99(6H, m).

IR(CHCl₃): 3446, 3004, 2952, 2874, 1709, 1652, 1515, 1485, 1305, 1153/cm.

[α]_(D)=−96.4° (CHCl₃, c=1.05, 23.0° C.).

No. 1k-4

CDCl₃ 300 MHz

1.05-2.17(14H, m), 2.38(2H, t, J=7.2 Hz), 2.52(1H, m), 3.81(1H, m), 5.33-5.50(2H, m), 6.08(1H, d, J=7.6 Hz), 7.39-7.53(3H, m), 7.57-7.62(6H, m).

IR(CHCl₃): 3420, 3250, 3008, 2948, 2870, 2660, 2208, 1735(sh), 1705, 1640, 1500/cm.

[α]_(D)=−21.9±0.6° (CHCl₃, c=1.02, 22° C.).

No. 1k-5

CDCl₃ 300 MHz

1.05-2.14(14H, m), 2.38(2H, t, J=7.2 Hz), 2.51(1H, m), 3.81(1H, m), 5.34-5.46(2H, m), 6.07(1H, d, J=7.6 Hz), 7.33-7.56(5H, m).

IR(CHCl₃): 3422, 3250, 3010, 2950, 2876, 2664, 2558, 2210, 1735(sh), 1705, 1645, 1502, 1441, 1410, 1307, 1276/cm.

[α]_(D)=−63.6±1.9° (CHCl₃, c=0.56, 22° C.).

No. 1k-6

CDCl₃ 300 MHz

1.04-2.24(14H, m), 2.36(2H, t, J=7.5 Hz), 2.58(1H, m), 3.88(1H, m), 5.30-5.43(2H, m), 6.21(1H, d, J=7.2 Hz), 7.41-7.49(3H, m), 7.73-7.77(2H, m).

IR(CHCl₃): 3447, 3011, 2955, 1708, 1653, 1603, 1578, 1515, 1486, 1457, 1312, 1211, 1164/cm.

[α]_(D)=−60.3° (CHCl₃, c=1.00, 23° C.).

No. 1k-7

CDCl₃ 300 MHz

1.04-2.22(14H, m), 2.36(2H, t, J=7.2 Hz), 2.57(1H, m), 3.87(1H, m), 5.30-5.44(2H, m), 6.17(1H, d, J=8.7 Hz), 6.99-7.40(7H, m), 7.73(2H, d, J=7.5 Hz).

IR(CHCl₃): 3449, 3013, 2955, 1739, 1708, 1651, 1609, 1588, 1522, 1487, 1243, 1227, 1169/cm.

[α]_(D)=−60.2° (CHCl₃, c=0.92, 23° C.).

No. 1k-8

CDCl₃ 300 MHz

1.04-2.25(14H, m), 2.34(2H, t, J=7.5 Hz), 2.56(1H, m), 3.87(1H, m), 5.30-5.44(2H, m), 6.19(1H, d, J=7.5 Hz), 6.83-6.94(6H, m), 7.69(2H, d, J=8.7 Hz).

IR(CHCl3): 3599, 3455, 3012, 2955, 1711, 1644, 1604, 1577, 1524, 1507, 1492, 1290, 1236, 1197, 1170/cm.

[α]_(D)=−47.7° (CHCl₃, C=1.01, 22° C.).

No. 1k-9

CDCl₃ 300 MHz

1.04-2.20(14H, m), 2.31(3H, s), 2.36(2H, t, J=7.2 Hz), 2.56 (1H, m), 3.86(1H, m), 5.30-5.43(2H, m), 6.16(1H, d, J=7.2 Hz), 7.00-7.11(6H, m), 7.74(2H, d, J=8.7 Hz).

IR(CHCl₃): 3450, 3010, 2955, 1750, 1709, 1651, 1609, 1596, 1523, 1489, 1370, 1247, 1227, 1183/cm.

[α]_(D)=−54.7° (CHCl₃, c=1.01, 22° C.).

No. 1k-10

CDCl₃ 300 MHz

1.04-2.22(14H, m), 2.35(2H, t, J=7.2 Hz), 2.56(1H, m), 3.82(3H, s), 3.86(1H, m), 5.30-5.43(2H, m), 6.17(1H, d, J=6.9 Hz), 6.89-7.01(6H, m), 7.70(2H, d, J=8.7 Hz).

IR(CHCl₃): 3023, 2955, 1742, 1708, 1649, 1613, 1602, 1577, 1522, 1507, 1490, 1227, 1210, 1170/cm.

[α]_(D)=−58.1° (CHCl₃, c=1.01, 22° C.).

No. 1m-1

CDCl₃ 300 MHz

1.06-2.25(14H, m), 2.32(2H, t, J=7.4 Hz), 2.61(1H, m), 3.63(3H, s), 3.91(1H, m), 5.33-5.47(2H, m), 6.24(1H, d, J=6.9 Hz), 7.35-7.38(3H, m), 7.53-7.60(4H, m), 7.75-7.78(2H, m).

IR(CHCl₃): 3438, 3008, 2946, 2875, 2212, 1732, 1650, 1605, 1519, 1496/cm.

[α]_(D)=+76° (CHCl₃, c=1.39, 24° C.)

No. 1m-2

CDCl₃ 300 MHz

1.05-2.20(14H, m), 2.36(2H, t, J=6.2 Hz), 2.59(1H, m), 3.89(1H, m), 5.29-5.48(2H, m), 6.26(1H, d, J=7.0 Hz), 7.26-7.38(3H, m), 7.52-7.60(4H, m), 7.73-7.77(2H, m).

IR(CHCl₃): 3444, 3012, 2952, 2874, 2664, 2214, 1718(sh), 1708, 1649, 1605, 1520, 1498/cm.

[α]_(D)=+81.4° (CHCl₃, c=1.01, 23° C.)

No. 1m-3

CDCl₃ 300 MHz

1.06-2.23(14H, m), 2.32(2H, t, J=7.0 Hz), 2.62(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.50(2H, m), 6.28(1H, d, J=7.0 Hz), 7.38-7.51(3H, m), 7.58-7.67(4H, m), 7.83-7.88(2H, m).

IR(CHCl₃): 3438, 3008, 2948, 2875, 1783(w), 1727, 1650, 1608, 1580(w), 1523, 1501, 1482/cm.

[α]_(D)=+59° (CHCl₃, c=1.49, 25° C.)

No. 1m-4

CDCl₃ 300 MHz

1.08-2.25(14H, m), 2.36(2H, t, J=7.4 Hz), 2.59(1H, m), 3.91(1H, m), 5.28-5.48(3H, m), 6.29(1H, d, J=7.4 Hz), 7.38-7.50(3H, m), 7.61-7.67(4H, m), 7.81-7.86(2H, m).

IR(CHCl₃): 3436, 3010, 2948, 2868, 1727, 1715(sh), 1649, , 1615(w), 1524, 1502, 1482, 1372/cm.

[α]_(D)=+72° (CHCl₃, c=0.98, 25° C.)

No. 1m-5

CDCl₃ 300 MHz

1.09-2.20(14H, m), 2.32(2H, t, J=7.2 Hz), 2.63(1H, m), 3.63(3H, s), 3.92(1H, m), 5.31-5.51(2H, m), 6.35(1H, d, J=7.0 Hz), 7.51-7.60(3H, m), 7.92-7.97(6H, m).

IR(CHCl₃): 3436, 3008, 2946, 2875, 1727, 1652, 1608(w), 1515, 1484/cm.

[α]_(D)=+82° (CHCl₃, c=0.99, 25° C.)

No. 1m-6

CDCl₃ 300 MHz

1.09-2.23(14H, m), 2.37(2H, t, J=7.2 Hz), 2.60(1H, m), 3.92(1H, m), 5.30-5.49(2H, m), 6.32(1H, d, J=7.4 Hz), 7.51-7.55(3H, m), 7.85-7.98(6H, m).

IR(CHCl₃): 3436, 3010, 2950, 2875, 2670, 1727, 1715(sh), 1650, 1605(w), 1515, 1484/cm.

[α]_(D)=+84° (CHCl₃, c=1.54, 25° C.)

No. 1m-7

CDCl₃ 300 MHz

1.03-2.18(14H, m), 2.32(2H, t, J=7.4 Hz), 2.59(1H, m), 3.64(3H, s), 3.89(1H, m), 5.29-5.49(2H, m), 6.16(1H, d, J=7.8 Hz), 6.98-7.06(4H, m), 7.14-7.20(1H, m), 7.34-7.41(2H, m), 7.73-7.78(2H, m).

IR(CHCl₃): 3438, 3008, 2946, 2868, 1727, 1648, 1610, 1586, 1519, 1485/cm.

[α]_(D)=+54° (CHCl₃, c=1.29, 25° C.).

No. 1m-8

CDCl₃ 300 MHz

1.06-2.21(14H, m), 2.36(2H, t, J=7.5 Hz), 2.58(1H, m), 3.88(1H, m), 5.31-5.46(2H, m), 6.17(1H, d, J=6.9 Hz), 6.99-7.05(4H, m), 7.15-7.21(1H, m), 7.36-7.41(2H, m), 7.72-7.75(2H, m).

IR(CHCl₃): 3436, 3010, 2948, 2868, 2675, 1730(sh), 1709, 1647, 1608, 1586, 1520, 1485/cm.

[α]_(D)=+56° (CHCl₃, c=0.97, 25° C.)

No. 1m-9

CDCl₃ 300 MHz

1.05-2.18(14H, m), 2.29-2.34(5H, m), 2.59(1H, m), 3.64(3H, s), 3.89(1H, m), 5.32-5.46(2H, m), 6.16(1H, d, J=7.5 Hz), 7.00-7.11(6H, m), 7.74-7.77(2H, m).

IR(CHCl₃): 3440, 3010, 2946, 2868, 1729, 1649, 1595, 1519, 1488/cm.

[α]_(D)=+47° (CHCl₃, c=0.82, 25° C.).

No. 1m-10

CDCl₃ 300 MHz

1.04-2.20(14H, m), 2.31-2.39(5H, m), 2.57(1H, m), 3.87(1H, m), 5.28-5.47(2H, m), 6.17(1H, d, J=7.0 Hz), 6.99-7.12(6H, m), 7.72-7.76(2H, m).

IR(CHCl₃): 3674, 3572, 3438, 3010, 2948, 2868, 2626, 1748, 1710, 1648, 1615, 1595, 1520, 1489/cm.

[α]_(D)=+51° (CHCl₃, c=0.91, 25° C.)

No. 1m-11

CDCl₃ 300 MHz

1.04-2.16(14H, m), 2.31(2H, t, J=7.2 Hz), 2.59(1H, m), 3.63(3H, s), 3.89(1H, m), 5.29-5.49(2H, m), 6.24(1H, d, J=7.4 Hz), 6.54(1H, s), 6.83-6.93(6H, m), 7.69-7.73(2H, m).

IR(CHCl₃): 3674, 3588, 3438, 3296, 3010, 2946, 2868, 1725, 1646, 1603, 1520, 1504, 1489/cm.

[α]_(D)=+51° (CHCl₃, c=0.91, 25° C.)

No. 1m-12

CDCl₃ 300 MHz

1.04-2.21(14H, m), 2.33(2H, t, J=8.0 Hz), 2.56(1H, m), 3.87(1H, m), 5.28-5.48(2H, m), 6.23(1H, d, J=8.0 Hz), 6.75(1H, m), 6.87-6.94(6H, m), 7.66-7.71(2H, m), 9.63(1H, brs).

IR(CHCl₃): 3674, 3582, 3436, 3275, 3010, 2950, 2868, 2675, 1727, 1710(sh), 1643, 1603, 1522, 1504, 1490/cm.

[α]_(D)=+30° (CHCl₃, c=0.97, 25° C.)

No. 1m-13

CDCl₃ 300 MHz

1.01-2.18(14H, m), 2.31(2H, t, J=7.4 Hz), 2.58(1H, m), 3.63(3H, s), 3.82(3H, s), 3.89(1H, m), 5.29-5.48(2H, m), 6.14(1H, d, J=7.0 Hz), 6.88-7.02(6H, m), 7.70-7.74(2H, m).

IR(CHCl₃): 3442, 3402, 3004, 2946, 2868, 1727, 1648, 1600, 1518, 1499/cm.

[α]_(D)=+42° (CHCl₃, c=1.82, 26° C.)

No. 1m-14

CDCl₃ 300 MHz

1.05-2.21(14H, m), 2.35(2H, t, J=7.2 Hz), 2.55(1H, m), 3.82(3H, s), 3.88(1H, m), 5.27-5.46(2H, m), 6.16(1H, d, J=7.2 Hz), 6.88-7.02(6H, m), 7.68-7.73(2H, m).

IR(CHCl₃): 3438, 3012, 2948, 2870, 2650, 1730(sh), 1709, 1647, 1615(sh), 1601, 1519, 1492/cm.

[α]_(D)=+64° (CHCl₃, c=0.70, 25° C.)

No. 1m-15

CDCl₃ 300 MHz

1.05-2.20(14H, m), 2.29-2.36(5H, m), 2.62(1H, m), 3.63(3H, s), 3.92(1H, m), 5.30-5.50(2H, m), 6.25(1H, d, J=7.2 Hz), 7.16-7.21(2H, m), 7.59-7.64(4H, m), 7.83-7.87(2H, m).

IR(CHCl₃): 3446, 3010, 2946, 2868, 1745(sh), 1728, 1650, 1615, 1525, 1507, 1486/cm.

[α]_(D)=+65.0° (CHCl₃, c=1.02, 23° C.)

No. 1m-16

CDCl₃ 300 MHz

1.08-2.21(14H, m), 2.34-2.40(5H, m), 2.59(1H, m), 3.90(1H, m), 5.29-5.48(2H, m), 6.29(1H, d, J=7.0 Hz), 7.18(2H, d, J=8.6 Hz), 7.58-7.64(4H, m), 7.83(2H, d, J=8.2 Hz).

IR(CHCl₃): 3438, 3012, 2948, 2870, 2622, 1749, 1710, 1649, 1610, 1526, 1508, 1487/cm.

[α]_(D)=+66° (CHCl₃, c=1.21, 24° C.)

No. 1m-17

CDCl₃ 300 MHz

1.06-2.19(14H, m), 2.32(2H, t, J=7.2 Hz), 2.62(1H, m), 3.63(3H, s), 3.93(1H, m), 5.30-5.50(2H, m), 6.32(1H, d, J=7.6 Hz), 6.41(1H, s), 6.94(2H, d, J=9.0 Hz), 7.47(2H, d, J=9.0 Hz), 7.58(2H, d, J=8.6 Hz), 7.81(2H, d, J=8.6 Hz).

IR(CHCl₃): 3580, 3434, 3284, 3010, 2946, 2868, 1726, 1646, 1606, 1528, 1490/cm.

[α]_(D)=+62.4° (CHCl₃, c=1.01, 23° C.)

No. 1m-18

CDCl₃+CD₃OD 300 MHz

1.11-2.18(14H, m), 2.32(2H, t, J=7.4 Hz), 2.59(1H, m), 3.88(1H, m), 5.30-5.49(2H, m), 6.5 5(1H, d, J=7.0 Hz), 6.92(2H, d, J=8.6 Hz), 7.47(2H, d, J=8.6 Hz), 7.59(2H, d, J=8.6 Hz), 7.79(2H, d, J=8.2 Hz).

IR(Nujol): 3398, 3175, 2725, 1696, 1635, 1601, 1531, 1510/cm.

[α]_(D)=+99.5° (CH₃OH, c=1.011, 25° C.)

No. 1m-19

CDCl₃ 300 MHz

1.05-2.20(14H, m), 2.32(2H, t, J=7.4 Hz), 2.61(1H, m), 3.63(3H, s), 3.86(3H, s), 3.94(1H, m), 5.30-5.50(2H, m), 6.24(1H, d, J=7.0 Hz), 6.99(2H, d, J=8.6 Hz), 7.53-7.63(4H, m), 7.82(2H, d, J=8.6 Hz).

IR(CHCl₃): 3440, 3006, 2946, 2875, 1726, 1649, 1606, 1527, 1510, 1489/cm.

[α]_(D)=+68° (CHCl₃, c=0.88, 26° C.)

No. 1m-20

CDCl₃ 300 MHz

1.09-2.20(14H, m), 2.35(2H, t, J=7.3 Hz), 2.58(1H, m), 3.85(3H, s), 3.89(1H, m), 5.28-5.48(2H, m), 6.35(1H, d, J=7.2 Hz), 6.98(2H, d, J=8.8 Hz), 7.51-7.61(4H, m), 7.81(2H, d, J=8.4 Hz), 8.34(1H, brs).

IR(CHCl₃): 3446, 3012, 2952, 2881, 2640, 1730(sh), 1707, 1647, 1606, 1527, 1510, 1489/cm.

[α]_(D)=+83° (CHCl₃, c=1.00, 25° C.).

No. 1m-21

CDCl₃ 300 MHz

1.05-2.14(14H, m), 2.37(2H, t, J=7.2 Hz), 2.51(1H, m), 3.81(1H, m), 5.34-5.46(2H, m), 6.11(1H, d, J=7.5 Hz), 7.33-7.48(3H, m), 7.53-7.55(2H, m).

IR(CHCl₃): 3420, 3250, 3008, 2948, 2870, 2660, 2210, 1735(sh), 1705, 1645, 1503, 1441, 1409/cm.

[α]_(D)=+59.2±1.0° (CHCl₃, c=1.023, 22° C.).

No. 1m-22

CDCl₃ 300 MHz

1.05-2.17(14H, m), 2.37(2H, t, J=7.2 Hz), 2.52(1H, m), 3.82(1H, m), 5.32-5.47(2H, m), 6.20(1H, d, J=7.6 Hz), 7.38-7.53(3H, m), 7.58-7.61(6H, m), 9.11(1H, brs).

IR(CHCl₃): 3420, 3250, 3010, 2984, 2870, 2675, 2208, 1730(sh), 1705, 1640, 1500, 1406/cm.

[α]_(D)=+57.4° (CHCl₃, c=1.83, 23° C.).

No. 1m-23

CDCl₃ 300 MHz

1.05-2.18(14H, m), 2.31(2H, t, J=7.5 Hz), 2.60(1H, m), 3.63(3H, s), 3.90(1H, m), 5.32-5.47(2H, m), 6.22(1H, d, J=6.9 Hz), 7.40-7.49(3H, m), 7.76-7.79(2H, m).

IR(CHCl₃): 3438, 3008, 2946, 2868, 1727, 1651, 1603, 1585, 1512, 1484/cm.

[α]_(D)=+52° (CHCl₃, c=1.49, 25° C.).

No. 1m-24

CDCl₃ 300 MHz

1.05-2.21(14H, m), 2.36(2H, t, J=7.2 Hz), 2.57(1H, m), 3.89(1H, m), 5.28-5.47(2H, m), 6.22(1H, d, J=7.0 Hz), 7.39-7.55(3H, m), 7.73-7.79(2H, m).

IR(CHCl₃): 3676, 3572, 3436, 3010, 2948, 2875, 1730(sh), 1709, 1650, 1600, 1580, 1514, 1484/cm.

[α]_(D)=+57° (CHCl₃, c=0.97, 26° C.).

No. 1m-25

CDCl₃ 300 MHz

1.04-2.18(14H, m), 2.28-2.35(5H, m), 2.59(1H, m), 3.62(3H, s), 3.88(1H, m), 5.29-5.49(2H, m), 6.20(1H, d, J=7.2 Hz), 7.15(2H, d, J=9.0 Hz), 7.80(2H, d, J=8.8 Hz).

IR(CHCl₃): 3436, 3010, 2946, 2868, 1752, 1727, 1653, 1602, 1519, 1491/cm.

[α]_(D)=+53° (CHCl₃, c=1.63, 25° C.).

No. 1m-26

CDCl₃ 300 MHz

1.05-2.19(14H, m), 2.32-2.38(5H, m), 2.56(1H, m), 3.88(1H, m), 5.29-5.47(2H, m), 6.25(1H, d, J=7.4 Hz), 7.15(2H, d, J=9.0 Hz), 7.78(2H, d, J=8.6 Hz).

IR(CHCl₃): 3434, 3016, 3006, 2948, 2880, 2622, 1752, 1730(sh), 1710, 1651, 1605, 1520, 1492/cm.

[α]_(D)=+58° (CHCl₃, c=3.68, 24C.)

No. 1m-27

CDCl₃ 300 MHz

1.05-2.16(14H, m), 2.30(2H, t, J=7.5 Hz), 2.57(1H, m), 3.62(3H, s), 3.87(1H, m), 5.27-5.47(2H, m), 6.32(1H, d, J=7.4 Hz), 6.85(2H, d, J=8.6 Hz), 7.62(2H, d, J=8.6 Hz), 8.35(1H, s).

IR(CHCl₃): 3580, 3450, 3216, 3010, 2946, 2868, 1726, 1640, 1608, 1584, 1528, 1496/cm.

[α]_(D)=+56.2° (CHCl₃, c=0.713, 23° C.)

No. 1m-28

CDCl₃ 200 MHz

1.10-2.25(14H, m), 2.32(2H, t, J=7.2 Hz), 2.55(1H, brs), 3.82-3.93(1H, m), 5.27-5.47(2H, m), 6.25(1H, d, J=7.4 Hz), 6.86(2H, d, J=8.6 Hz), 7.62(2H, d, J=8.6 Hz).

IR(CHCl₃): 3438, 3242, 2675, 1730(sh), 1708, 1639, 1607, 1585/cm.

No. 1m-29

CDCl₃ 300 MHz

1.05-2.18(14H, m), 2.31(2H, t, J=7.4 Hz), 2.58(1H, m), 3.64(3H, s), 3.85(3H, s), 3.89(1H, m), 5.29-5.48(2H, m), 6.14(1H, d, J=6.6 Hz), 6.92(2H, d, J=9.0 Hz), 7.74(2H, d, J=9.0 Hz).

IR(CHCl₃): 3445, 3008, 2946, 2868, 1727, 1646, 1606, 1578, 1523, 1493/cm.

[α]_(D)=+53° (CHCl₃, c=2.03, 24° C.)

No. 1m-30

CDCl₃ 300 MHz

1.04-2.21(14H, m), 2.36(2H, t, J=7.3 Hz), 2.56(1H, m), , 3.85(3H, s), 3.88(1H, m), 5.27-5.46(2H, m), 6.15(1H, d, J=7.2 Hz), 6.92(2H, d, J=8.6 Hz), 7.73(2H, d, J=8.6 Hz)

IR(CHCl₃): 3440, 3010, 2950, 2870, 2645, 1727, 1710(sh), 1646, 1606, 1575, 1524, 1494/cm.

[α]_(D)=+62° (CHCl₃, c=1.10, 24° C.).

No. 1m-31

CDCl₃+CD₃OD 300 MHz

1.16-2.20(14H, m), 2.31(2H, t, J=7.2 Hz), 2.59(1H, m), 3.85(1H, m), 5.31-5.51(2H, m), 7.13-7.21(1H, m), 7.31-7.42(2H, m), 7.68-7.93(6H, m).

IR(Nujol): 3344, 3175, 2715, 2675, 1699, 1631, 1566/cm.

[α]_(D)=+67° (CH₃OH, c=1.01, 24° C.).

No. 1m-32

CDCl₃ 200 MHz

1.09-2.23(14H, m), 2.33(2H, t, J=7.1 Hz), 2.57(1H, brs), 3.40-3.93(9H, m), 4.41(1H, brs), 5.29-5.48(2H, m), 6.44(1H, d, J=7.4 Hz), 7.43(2H, d, J=8.2 Hz), 7.80(2H, d, J=7.8 Hz).

IR(CHCl₃): 3434, 3354, 1726, 1720(sh), 1660(sh), 1626/cm.

No. 1m-33

CDCl₃ 200 MHz

1.14-2.25(14H, m), 2.37(2H, t, J=7.3 Hz), 2.64(1H, brs), 3.93-4.01(1H, m), 5.30-5.51(2H, m), 6.47(1H, d, J=7.4 Hz), 7.63-7.74(2H, m), 7.79(2H, s), 7.89-7.93(1H, m), 8.00(1H, dd, J=2.3, 1.0 Hz), 8.30(1H, d, J=1.0 Hz), 8.65-8.73(2H, m).

IR(CHCl₃): 3450, 2675, 1728, 1707, 1649, 1528, 1509/cm.

[α]_(D)=+82.8±1.2° (CHCl₃, c=1.01, 23° C.).

No. 2a-1

[α]_(D)=+69.0° (MeOH, c=1.01, 25° C.)

No. 2a-2

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 4.30(1H, m), 5.35-5.52(2H, m), 6.32(1H, d, J=8.7 Hz), 7.36-7.49(3H, m), 7.58-7.62(2H, m), 7.66 and 7.80(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3116, 3014, 2925, 2870, 2663, 1708, 1651, 1610, 1524, 1504, 1484, 1472/cm.

[α]_(D)=+64.1° (MeOH, c=1.02, 25° C.).

No. 2a-3

[α]_(D)=+76.6° (MeOH, c=1.18, 26° C.).

No. 2a-4

CDCl 300 MHz

0.99(1H, d, J=10.2 Hz), 1.15 and 1.25(each 3H, each s), 1.64-2.51(14H, m), 4.31(1H, m), 5.36-5.53(2H, m), 6.33(1H, d, J=8.4 z), 7.50-7.56(3H, m), 7.85-7.98(6H, m).

IR(CHCl₃): 3515, 3452, 3014, 2925, 2870, 1740, 1708, 1654, 1517, 1486, 1470/cm.

[α]_(D)=+79.5° (MeOH, c=1.18, 22° C.).

No. 2a-5

CD₃OD 300 MHz

0.98(1H, d, J=9.9 Hz), 1.18 and 1.25(each 3H, each s), 1.56-1.71(3H, m), 1.98-2.40(11H, m), 4.17(1H, m), 5.41-5.52(2H, m), 7.52-7.61(3H, m), 7.91-8.01(6H, m).

IR(KBr): 3416, 3063, 2983, 2921, 2869, 1704, 1643, 1566, 1518, 1488, 1408/cm.

[α]_(D)=+62.0° (MeOH, c=1.00, 25° C.).

No. 2a-6

[α]_(D)=+64.1° (MeOH, c=1.01, 25° C.).

No. 2a-7

[α]_(D)=+65.3° (MeOH, c=0.99, 25° C.).

No. 2a-8

[α]_(D)=+74.0° (MeOH, c=1.01, 25° C.).

No. 2a-9

[α]_(D)=+71.0° (MeOH, c=1.10, 25° C.).

No. 2a-10

[α]_(D)=+74.7° (MeOH, c=1.00, 25° C.).

No. 2a-11

[α]_(D)=+72.1° (MeOH, c=1.00, 25° C.).

No. 2a-12

[α]_(D)=+53.1° (CHCl₃, c=1.01, 26° C.).

m.p. 155.0-156.0° C.

No. 2a-13

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.18 and 1.25(each 3H, each s), 1.63-2.40(14H, m), 4.30(1H, m), 5.46-5.58(2H, m), 6.44(1H, d, J=8.4 Hz), 7.49 and 7.77(each 2H, each d, J=8.7 Hz), 7.54(1H, s).

IR(CHCl₃): 3689, 3378, 3028, 3014, 2924, 1713, 1652, 1602, 1522, 1496/cm.

[α]_(D)=+78.3° (MeOH, c=0.84, 25° C.).

m.p. 205.0-206.0° C.

No. 2a-14

[α]_(D)=+72.5° (MeOH, c=1.07, 25° C.).

No. 2a-15

CDCl₃ 300 MHz

0.99(1H, d, J=9.9 Hz), 1.14 and 1.24(each 3H, each s), 1.55-2.44(14H, m), 4.27(1H, m), 5.30-5.50(2H, m), 6.29(1H, d, J=9.0 Hz), 7.11 and 7.20(each 1H, each d, J=16.2 Hz), 7.29-7.55(5H, m), 7.57 and 7.72(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3453, 3083, 3022, 3013, 2925, 2870, 1708, 1650, 1607, 1560, 1522, 1496/cm.

[α]_(D)=+72.3° (MeOH, c=1.00, 27° C.).

m.p. 115.0-117.0° C.

No. 2a-16

CDCl₃ 300 MHz

0.92(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.48(14H, m), 3.62(3H, s), 4.29(1H, m), 5.30-5.50(2H, m), 6.20(1H, d, J=8.7 Hz), 6.59 and 6.68(each 1H, each, d, J=12.3 Hz), 7.23(5H, s), 7.29 and 7.59(each 2H, each d, J=8.1 Hz).

IR(CHCl₃): 3453, 3024, 3016, 2924, 2870, 1730, 1651, 1607, 1520, 1495/cm.

[α]_(D)=+56.8° (MeOH, c=1.04, 24° C.).

No. 2a-17

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.38(14H, m), 4.26(1H, m), 5.30-5.50(2H, m), 6.23(1H, d, J=8.4 Hz), 6.59 and 6.70(each 1H, each d, J=12.3 Hz), 7.23(5H, s), 7.30 and 7.57(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3452, 3081, 3019, 3014, 2925, 2870, 2665, 1708, 1650, 1607, 1521, 1495/cm.

[α]_(D)=+61.6° (MeOH, c=1.00, 27° C.).

No. 2a-18

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each, s), 1.50-2.50(14H, m), 3.61(3H, s), 4.31(1H, m), 5.35-5.51(2H, m), 6.33(1H, d, J=8.4 Hz), 7.48-7.64(4H, m), 7.79-7.83(2H, m), 7.91(1H, dt, J=1.5 and 7.8 Hz), 8.01(1H, dt, J=1.5 and 7.8 Hz), 8.13(1H, t, J=1.5 Hz).

IR(CHCl₃): 3450, 3026, 3013, 2925, 2870, 1730, 1659, 1600, 1510/cm.

[α]_(D)=+56.0° (MeOH, c=1.01, 25° C.).

No. 2a-19

CDCl₃ 300 MHz

0.95(1H, d, J=9.9 Hz), 1.14 and 1.21(each 3H, each s), 1.53-2.60(14H, m), 4.25(1H, m), 5.35-5.64(2H, m), 7.21(1H, d, J=7.8 Hz), 7.49-7.68(4H, m), 7.76-7.84(3H, m), 8.25(1H, m), 8.43(1H, m).

IR(CHCl₃): 3382, 3196, 3025, 3015, 2925, 2870, 1725, 1652, 1599, 1577, 1521/cm.

[α]_(D)=+55.9° (MeOH, c=1.00, 25° C.).

No. 2a-20

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.13 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 3.62(3H, s), 4.31(1H, m), 5.35-5.51(2H, m), 6.24(1H, d, J=8.4 Hz), 7.40-7.52(3H, m), 7.71-7.76(2H, m).

IR(CHCl₃): 3453, 3025, 3013, 2925, 2870, 1730, 1753, 1579, 1514, 1486/cm.

[α]_(D)=+61.2° (MeOH, c=1.04, 25° C.).

No. 2a-21

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.28(1H, m), 5.34-5.51(2H, m), 6.27(1H, d, J=8.7 Hz), 7.41-7.53(3H, m), 7.71-7.74(2H, m).

IR(CHCl₃): 3452, 3063, 3027, 3014, 2925, 2871, 1708, 1652, 1578, 1515, 1486/cm.

[α]_(D)=+62.0° (MeOH, c=1.01, 27° C.).

No. 2a-22

d₆-DMSO 300 MHz

0.86(1H, d, J=9.9 Hz), 1.10 and 1.16(each 3H, each s), 1.42-1.52(3H, m), 1.85-2.46(11H, m), 3.98(1H, m), 5.32-5.43(2H, m), 7.41(3H, m), 7.88(2H, d, J=6.6 Hz), 8.19(1H, d, J=6.6 Hz).

IR(KBr): 3367, 3060, 2984, 2922, 2868, 1634, 1563, 1529, 1487/cm.

[α]_(D)=+47.7° (MeOH, c=1.00, 25° C.).

No. 2a-23

[α]_(D)=+62.7° (MeOH, c=1.01, 27° C.).

No. 2a-24

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.14 and 1.25(each 3H, each s), 1.52-2.50(14H, m), 4.31(1H, m), 5.36-5.52(2H, m), 6.34(1H, d, J=8.4 Hz), 7.47-7.52(2H, m), 7.59-7.64(1H, m), 7.78-7.83(6H, m).

IR(CHCl₃): 3449, 3027, 3013, 2925, 2869, 1708, 1656, 1599, 1518, 1493/cm.

[α]_(D)=+63.1° (MeOH, c=1.00, 25° C.).

No. 2a-25

[α]_(D)=+35.1° (MeOH, c=1.00, 25° C.).

No. 2a-26

[α]_(D)=+35.5° (MeOH, c=1.02, 25° C.).

No. 2a-27

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 3.63(3H, s), 4.29(1H, m), 5.36-5.51(2H, m), 6.18(1H, d, J=8.4 Hz), 7.01 and 7.71(each 2H, each d, J=8.7 Hz), 6.98-7.05(2H, m), 7.16(1H, t, J=7.5 Hz), 7.34-7.41(2H, m).

IR(CHCl₃): 3455, 3024, 3016, 2924, 2870, 1730, 1651, 1588, 1520, 1487/cm.

[α]_(D)=+56.4° (MeOH, c=1.01, 25° C.).

No. 2a-28

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.26(1H, m), 5.34-5.51(2H, m), 6.20(1H, d, J=9.0 Hz), 7.01 and 7.70(each 2H, each d, J=9.0 Hz, ), 6.98-7.15(2H, m), 7.17(1H, t, J=7.5 Hz), 7.34-7.40(2H, m).

IR(CHCl₃): 3454, 3031, 3018, 2925, 2870, 1708, 1650, 1588, 1523, 1487/cm.

[α]_(D)=+56.2° (MeOH, c=1.00, 25° C.).

No. 2a-29

[α]_(D)=+53.0° (MeOH, c=1.03, 25° C.).

No. 2a-30

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.25(1H, m), 5.30-5.50(2H, m), 6.23(1H, d, J=8.7 Hz), 6.36(1H, s), 7.26-7.39(10H, m), 7.60 and 7.68(each 2H, each d, J=8.4 Hz, ).

IR(CHCl₃): 3451, 3088, 3064, 3029, 3014, 2925, 2869, 1707, 1652, 1522, 1495/cm.

[α]_(D)=+54.2° (MeOH, c=1.00, 25° C.).

No. 2a-31

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 3.63(3H, s), 4.31(1H, m), 5.30-5.50(2H, m), 6.26(1H, d, J=8.4 Hz), 6.90(1H, t, J=7.4 Hz), 7.13(1H, d, J=8.7 Hz), 7.29(2H, t, J=8.0 Hz), 7.67-7.75(5H, m), 7.82(1H, s).

IR(Nujol): 3380, 3244, 1723, 1638, 1601, 1578, 1535, 1495/cm.

[α]_(D)=+73.6° (MeOH, c=0.50, 26° C.).

m.p. 133.0-134.0° C.

No. 2a-32

[α]_(D)=+56.1° (MeOH, c=1.02, 26° C.).

No. 2a-33

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.10 and 1.21(each, 3H, each s), 1.50-2.50(14H, m), 4.25(1H, m), 5. 13(2H, s), 5.30-5.70(3H, m), 6.41(1H, d, J=8.2 Hz), 6.89(1H, s), 7.09(1H, s), 7.17 and 7.72(each 2H, each d, J=8.2 Hz), 7.62(1H, s).

IR(CHCl₃): 3450, 3125, 3031, 3013, 2925, 2870, 2467, 1917, 1708, 1654, 1615, 1575, 1523, 1497/cm.

[α]_(D)=+55.2° (MeOH, c=1.01, 26° C.).

No. 2a-34

[α]_(D)=+72.9° (MeOH, c=1.03, 25° C.).

No. 2a-35

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.13 and 1.24(each 3H, each s), 1.52-2.48(14H, m), 4.28(1H, m), 5.35-5.51(2H, m), 6.28(1H, d, J=8.7 Hz), 7.34-7.37(3H, m), 7.52-7.55(2H, m), 7.58 and 7.71(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3515, 3452, 3030, 3012, 2925, 2870, 1739, 1708, 1652, 1607, 1555, 1521, 1497/cm.

[α]_(D)=+74.3° (MeOH, c=1.01, 25° C.).

No. 2a-36

[α]_(D)=+23.4° (MeOH, c=1.07, 25° C.).

No. 2a-37

CDCl₃ 300 MHz

0.83(1H, d, J=10.5 Hz), 0.95 and 1.18(each 3H, each s), 1.44-2.46(14H, m), 3.92(1H, m), 5.34-5.52(3H, m), 7.26-7.54(9H, m), 7.62(1H, s).

IR(CHCl₃): 3432, 3310, 3189, 3023, 3014, 2924, 2870, 1704, 1610, 1594, 1523, 1487/cm.

[α]_(D)=+25.3° (MeOH, c=1.00, 26° C.).

No. 2a-38

[α]_(D)=+70.9° (MeOH, c=1.02, 25° C.).

No. 2a-39

[α]_(D)=+70.6° (MeOH, c=1.01, 25° C.).

No. 2a-40

[α]_(D)=+74.7° (MeOH, c=1.00, 25° C.).

No. 2a-41

[α]_(D)=+72.1° (MeOH, c=1.01, 24° C.).

No. 2a-42

[α]_(D)=+69.2° (MeOH, c=1.00, 25° C.).

No. 2a-43

[α]_(D)=+70.8° (MeOH, c=1.00, 25° C.).

No. 2a-44

[α]_(D)=+60.4° (MeOH, c=1.00, 26° C.).

No. 2a-45

CDCl₃ 300 MHz

0.97(1H, d, J=9.9 Hz), 1.13 and 1.23(each 3H, each s), 1.55-2.52(14H, m), 4.29(1H, m), 5.34-5.54(2H, m), 6.33(1H, d, J=9.0 Hz), 7.10(1H, t, J=7.4 Hz), 7.34(2H, t, J=7.4 Hz), 7.52(2H, m), 7.68 and 7.75(each 2H, each d, J=8.4 Hz), 7.80(1H, s), 8.10(1H, s), 10.09(1H, s).

IR(CHCl₃): 3393, 3195, 3093, 3033, 3013, 2925, 2870, 1698, 1656, 1598, 1537, 1498/cm.

[α]_(D)=+59.4° (MeOH, c=1.01, 24° C.).

No. 2a-46

[α]_(D)=+63.5° (MeOH, c=1.00, 25° C.).

No. 2a-47

CDCl₃ 300 MHz

0.97(1H, d, J=9.9 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 4.29(1H, m), 5.35-5.52(2H, m), 6.32(1H, d, J=8.7 Hz), 7.26(1H, m), 7.41(2H, t, J=7.8 Hz), 7.64(2H, d, J=7.5 Hz), 7.73 and 7.77(each 2H, each d, J=8.4 Hz), 7.95(1H, s), 9.20(1H, s), 10.38(1H, s).

IR(CHCl₃): 3450, 3339, 3003, 2992, 2925, 2870, 1706, 1653, 1596, 1523, 1495/cm.

[α]_(D)=+63.3° (MeOH, c=1.00, 25° C.).

No. 2a-48

[α]_(D)=+63.8° (MeOH, c=1.00, 24° C.).

No. 2a-49

CDCl₃ 300 MHz

1.00(1H, d, J=10.5 Hz), 1.17 and 1.26(each 3H, each s), 1.55-2.52(14H, m), 4.34(1H, m), 5.36-5.54(2H, m), 6.35(1H, d, J=9.0 Hz), 7.50-7.62(3H, m), 7.90 and 8.33(each 2H, each d, J=8.4 Hz), 8.21(2H, m).

IR(CHCl₃): 3451, 3029, 3022, 3016, 2925, 2870, 1708, 1655, 1542, 1508, 1498, 1471, 1459/cm.

[α]_(D)=+63.5° (MeOH, c=1.02, 25° C.).

m.p. 135.0-137.0° C.

No. 2a-50

[α]_(D)=+68.9° (MeOH, c=1.01, 24° C.).

No. 2a-51

d₆-DMSO 300 MHz

0.87(1H, d, J=9.9 Hz), 1.10 and 1.17(each 3H, each s), 1.40-1.60(3H, m), 1.90-2.40(11H, m), 3.98(1H, m), 5.35-5.46(2H, m), 7.64(1H, s), 7.65 and 7.91(each 2H, each d, J=8.7 Hz), 8.06(1H, d, J=6.0 Hz), 9.32(1H, brs).

IR(KBr): 3385, 2962, 1734, 1707, 1632, 1529, 1498/cm.

[α]_(D)=+68.4° (MeOH, c=1.01, 24° C.).

No. 2a-52

[α]_(D)=+76.2° (MeOH, c=1.01, 24° C.).

No. 2a-53

[α]_(D)=+73.9° (MeOH, c=1.02, 24° C.).

No. 2a-54

[α]_(D)=+68.1° (MeOH, c=1.00, 24° C.).

No. 2a-55

[α]_(D)=+67.8° (MeOH, c=1.00, 24° C.).

No. 2a-56

[α]_(D)=+65.4° (MeOH, c=1.03, 25° C.).

No. 2a-57

[α]_(D)=+63.4° (MeOH, c=1.01, 24° C.).

No. 2a-58

[α]_(D)=+66.6° (MeOH, c=1.01, 24° C.).

No. 2a-59

[α]_(D)=+65.5° (MeOH, c=1.00, 24° C.).

No. 2a-60

[α]_(D)=+60.9° (MeOH, c=1.02, 25° C.).

No. 2a-61

CDCl₃ 300 MHz

0.97(1H, d, J=10.0 Hz), 1.10 and 1.22(each 3H, each s), 1.50-2.50(14H, m), 4.26(1H, m), 5.30-5.54(2H, m), 6.28(1H, d, J=8.6 Hz), 6.60 and 6.82(each 1H, each d, J=12.4 Hz, ), 7.12(2H, d, J=6.0 Hz), 7.25 and 7.62(each 2H, each d, J=8.6 Hz), 8.47(2H, d, J=6.0 Hz).

IR(CHCl₃): 3452, 3027, 3019, 3013, 2925, 2870, 2480, 1708, 1651, 1606, 1520, 1494/cm.

[α]_(D)=+61.6° (MeOH, c=1.01, 25° C.).

No. 2a-62

[α]_(D)=+72.0° (MeOH, c=0.93, 25° C.).

No. 2a-63

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 4.29(1H, m), 5.36-5.55(2H, m), 6.35(1H, d, J=9.1 Hz), 7.04 and 7.27(each 1H, each d, J=16.5 Hz), 7.37(2H, d, J=6.6 Hz), 7.56 and 7.76(each 2H, each d, J=8.4 Hz), 8.57(2H, d, J=6.6 Hz).

IR(CHCl₃): 3452, 3024, 3018, 3014, 2925, 2870, 2470, 1933, 1708, 1652, 1605, 1521, 1496/cm.

[α]_(D)=+69.2° (MeOH, c=1.01, 25° C.).

No. 2a-64

[α]_(D)=+56.9° (MeOH, c=1.24, 25° C.).

No. 2a-65

CDCl₃ 300 MHz

0.98(1H, d, J=10.5 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.46(14H, m), 4.27(1H, m), 5.23(2H, s), 5.34-5.52(2H, m), 6.26(1H, d, J=8.4 Hz), 7.32-7.45(5H, m), 7.64 and 7.71(each 2H, each d, J=8.4 Hz), 8.15(1H, s).

IR(CHCl₃): 3452, 3088, 3065, 3032, 3013, 2925, 2870, 1708, 1653, 1611, 1559, 1522, 1496/cm.

[α]_(D)=+61.0° (MeOH, c=0.91, 25° C.).

No. 2a-66

[α]_(D)=+76.0° (MeOH, c=1.01, 25° C.).

No. 2a-67

CDCl₃ 300 MHz

0.98(1H, d, J=10.4 Hz), 1.14 and 1.24(each 3H, each s), 1.54-2.46(14H, m), 4.28(1H, m), 5.32-5.53(2H, m), 6.27(1H, d, J=8.6 Hz), 6.92-7.31(each 1H, each d, J=16.4 Hz), 7.02(1H, dd, J=5.8 and 3.6 Hz), 7.12(1H, d, J=3.6 Hz), 7.24(1H, d, J=5.8 Hz), 7.51 and 7.70(each 2H, each d, J=8.4 Hz).

IR(CHCl₃): 3453, 3029, 3013, 2925, 2870, 1739, 1650, 1604, 1524, 1515, 1494/cm.

[α]_(D)=+76.2° (MeOH, c=1.00, 24° C.).

m.p. 104.0-106.0° C.

No. 2a-68

[α]_(D)=+57.7° (MeOH, c=1.01, 25° C.).

No. 2a-69

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 4.28(1H, m), 5.34-5.53(2H, m), 6.29(1H, d, J=9.0 Hz), 6.54-6.74(each 1H, each d, J=12.0 Hz), 7.02(1H, dd, J=4.8 and 3.3 Hz), 6.97(1H, dd, J=3.3 and 1.2 Hz), 7.13(1H, dd, J=4.8 and 1.2 Hz), 7.44 and 7.70(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3453, 3025, 3010, 2925, 2870, 1708, 1650, 1607, 1559, 1523, 1493/cm.

[α]_(D)=+58.4° (MeOH, c=1.00, 25° C.).

No. 2a-70

[α]_(D)=+48.6° (MeOH, c=1.00, 25° C.).

No. 2a-71

CDCl₃ 300 MHz 0.98(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.31(3H, s), 4.26(1H, m), 5.33-5.52(2H, m), 6.20(1H, d, J=9.3 Hz), 7.02-7.11(6H, m), 7.70(2H, d, J=9.0 Hz).

IR(CHCl₃): 3460, 3031, 3022, 3011, 2925, 2870, 1750, 1708, 1650, 1608, 1597, 1523, 1490/cm.

[α]_(D)=+48.9° (MeOH, c=1.01, 25° C.).

No. 2a-72

[α]_(D)=+51.2° (MeOH, c=1.02, 25° C.).

No. 2a-73

CDCl₃ 300 MHz

0.97(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 4.27(1H, m), 5.32-5.52(2H, m), 6.24(1H, d, J=9.0 Hz), 6.83-6.94(6H, m), 7.65(2H, d, J=9.0 Hz).

IR(CHCl₃): 3598, 3451, 3199, 3033, 3012, 2925, 2870, 1708, 1642, 1604, 1524, 1507, 1491/cm.

[α]_(D)=+52.2° (MeOH, c=1.01, 25° C.).

No. 2a-74

[α]_(D)=+51.5° (MeOH, c=0.92, 25° C.).

No. 2a-75

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.55-2.46(14H, m), 3.82(3H, s), 4.25(1H, m), 5.32-5.52(2H, m), 6.19(1H, d, J=8.7 Hz), 6.89-7.01(6H, m), 65-7.68(2H, m).

IR(CHCl₃): 3450, 3025, 3008, 2925, 2870, 2837, 1741, 1649, 1612, 1521, 1505, 1490/cm.

[α]_(D)=+51.1° (MeOH, c=1.00, 25° C.).

No. 2a-76

[α]_(D)=+60.4° (MeOH, c=0.98, 25° C.).

No. 2a-77

CDCl₃ 300 MHz

0.99(1H, d, J=10.5 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 2.34(3H, s), 4.29(1H, m), 5.32-5.54(2H, m), 6.32(1H, d, J=8.4 Hz), _(7.19) each 2H, each d, J=8.4 Hz), 7.63 and 7.79(each 2H, each d, J=8.4 Hz).

IR(CHCl₃): 3452, 3027, 3012, 2925, 2870, 1751, 1709, 1651, 1611, 1560, 1527, 1509, 1489/cm.

[α]_(D)=+61.2° (MeOH, c=1.00, 25° C.).

No. 2a-78

[α]_(D)=+67.4° (MeOH, c=1.01, 25° C.).

No. 2a-79

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.54(14H, m), 4.31(1H, m), 5.32-5.54(2H, m), 6.36(1H, d, J=8.2 Hz), 6.93 and 7.48(each 2H, each d, J=8.6 Hz), 7.59 and 7.75(each 2H, each d, J=8.4 Hz).

IR(CHCl₈): 3593, 3448, 3192, 3030, 3010, 2925, 2870, 1708, 1644, 1608, 1591, 1559, 1530, 1516, 1491/cm.

[α]_(D)=+65.8° (MeOH, c=1.01, 25° C.).

No. 2a-80

[α]_(D)=+66.9° (MeOH, c=1.01, 25° C.).

No. 2a-81

CDCl₃ 300 MHz

0.99(1H, d, J=10.5 Hz), 1.15 and 1.24(each 3H, each s), 1.54-2.48(14H, m), 3.86(3H, s), 4.29(1H, m), 5.34-5.52(2H, m), 6.20(1H, d, J=8.7 Hz), 6.99 and 7.55 each 2H, each d, J=9.0 Hz), 7.61 and 7.77(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3450, 3009, 2925, 2870, 2838, 1740, 1708, 1650, 1608, 1557, 1528, 1512, 1491/cm.

[α]_(D)=+66.2° (MeOH, c=1.01, 25° C.).

No. 2a-82

[α]_(D)=+57.7° (MeOH, c=1.02, 24° C.).

No. 2a-83

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 2.33(3H, s), 4.26(1H, m), 5.32-5.52(2H, m), 6.25(1H, d, J=8.7 Hz), 7.16 and 7.75(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3452, 3030, 3022, 3012, 2925, 2870, 1754, 1709, 1654, 1604, 1585, 1522, 1493/cm.

[α]_(D)=+57.4° (MeOH, c=1.01, 24° C.).

No. 2a-84

[α]_(D)=+57.8° (MeOH, c=1.01, 24° C.).

No. 2a-85

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.54-2.48(14H, m), 4.25(1H, m), 5.32-5.52(2H, m), 6.28(1H, d, J=8.7 Hz), 6.87 and 7.57(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3590, 3450, 3166, 3019, 3012, 2925, 2871, 1708, 1637, 1608, 1583, 1531, 1498/cm.

[α]_(D)=+56.0° (MeOH, c=1.01, 24° C.).

No. 2a-86

[α]_(D)=+59.3° (MeOH, c=1.01, 22° C.).

No. 2a-87

CDCl₃ 300 MHz

0.98(1H, d, J=10.0 Hz), 1.13 and 1.23(each 3H, each s), 1.54-2.48(14H, m), 3.85(3H, s), 4.25(1H, m), 5.32-5.53(2H, m), 6.19(1H, d, J=8.8 Hz), 6.93 and 7.69(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3450, 3030, 3017, 3012, 2925, 2870, 2840, 1740, 1708, 1647, 1606, 1575, 1525, 1496/cm.

[α]_(D)=+58.2° (MeOH, c=0.99, 22° C.).

No. 2a-88

[α]_(D)=+50.9° (MeOH, c=1.02, 25° C.).

No. 2a-89

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.18 and 1.26(each 3H, each s), 1.56-2.48(14H, m), 4.29(1H, m), 5.36-5.54(2H, m), 7.03(1H, d, J=8.7 Hz), 7.21(1H, s), 7.43(2H, m), 7.74(1H, ddd, J=1.8, 6.9 and 8.7 Hz), 8.22(1H, dd, J=1.8 and 8.1 Hz).

IR(CHCl₃): 3443, 3087, 3023, 3014, 2925, 2870, 1708, 1685, 1658, 1630, 1517, 1466/cm.

[α]_(D)=+57.10(MeOH, c=1.01, 22° C.).

m.p. 117.0-118.0° C.

No. 2a-90

[α]_(D)=+54. 1° (MeOH, c=1.01, 22° C.).

No. 2a-91

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.24(1H, m), 5.34-5.52(2H, m), 6.49-6.53(2H, m), 7.11(1H, dd, J=0.9 and 3.6 Hz), 7.44(1H, dd, J=0.9 and 1.8 Hz).

IR(CHCl₃): 3437, 3033, 3022, 3014, 2925, 2870, 1739, 1708, 1655, 1595, 1520, 1472/cm.

[α]_(D)=+55.0° (MeOH, c=1.00, 22° C.).

No. 2a-92

[α]_(D)=+50.3° (MeOH, c=1.00, 22° C.).

No. 2a-93

CDCl₃ 300 MHz

0.95(1H, d, J=10.5 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.34-5.52(2H, m), 6.12(1H, d, J=8.7 Hz), 7.07(1H, dd, J=3.9 and 5.1 Hz), 7.45-7.48(2H, m).

IR(CHCl₃): 3450, 3023, 3011, 2925, 2870, 1739, 1708, 1645, 1531, 1501, 1471/cm.

[α]_(D)=+49.1° (MeOH, c=1.02, 24° C.).

No. 2a-94

[α]_(D)=+51.5° (MeOH, c=1.00, 24° C.).

No. 2a-95

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.34-5.56(2H, m), 6.14(1H, d, J=8.7 Hz), 7.34(2H, d, J=2.0 Hz), 7.85(1H, t, J=2.0 Hz).

IR(CHCl₃): 3452, 3114, 3030, 3013 2925, 2870, 1708, 1649, 1535, 1498, 1471/cm.

[α]_(D)=+55.5° (MeOH, c=1.00, 25° C.).

m.p .87.0-88.0° C.

No. 2a-96

CDCl₃ 300 MHz

0.94(1H, d, J=10.2 Hz), 1.13 and 1.22(each 3H, each s), 1.50-1.76(3H, m), 1.94-2.39(11H, m), 4.11(1H, m), 5.39-5.49(2H, m), 7.43-7.51(2H, m), 8.05(1H, m).

IR(KBr): 3369, 3084, 2985, 2921, 2868, 1630, 1566, 1538, 1503/cm.

[α]_(D)=+38.8° (MeOH, c=1.01, 22° C.).

No. 2a-97

CD₃OD 300 MHz

0.93(1H, d, J=9.9 Hz), 1.13 and 1.22(each 3H, each s), 1.48-1.58(3H, m), 1.96-2.36(11H, m), 4.10(1H, m), 5.35-5.50(2H, m), 7.42-7.51(2H, m), 8.06(1H, m).

IR(KBr): 3447, 3087, 2987, 2922, 2868, 1629, 1545, 1501/cm.

[α]_(D)=+52.9° (MeOH, c=1.01, 24° C.).

No. 2a-98

[α]_(D)=+53.2° (MeOH, c=1.02, 23° C.).

No. 2a-99

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.26-2.45(24H, m), 4.25(2H, m), 5.34-5.52(2H, m), 6.18(1H, d, J=8.7 Hz), 6.91 and 7.66(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3455, 3029, 3019, 2939, 2862, 1738, 1709, 1645, 1605, 1523, 1494/cm.

[α]_(D)=+51.4° (MeOH, c=1.00, 23° C.).

No. 2a-100

[α]_(D)=+49.3° (MeOH, c=1.00, 24° C.).

No. 2a-101

[α]_(D)=+51.3° (MeOH, c=1.00, 24° C.).

No. 2a-102

[α]_(D)=+48.8° (MeOH, c=1.01, 23° C.).

No. 2a-103

CDCl₃ 300 MHz

0.94(1H, d, J=10.2 Hz), 1.12 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 2.48(3H, d, J=0.3 Hz), 4.20(1H, m), 5.32-5.54(2H, m), 6.46(1H, brs), 7.12(1H, d, J=9.0 Hz).

IR(CHCl₃): 3415, 3144, 3029, 3011, 2926, 2871, 1708, 1671, 1598, 1538, 14564/cm

[α]_(D)=+49.6° (MeOH, c=1.01, 23° C.).

No. 2a-104

[α]_(D)=+77.0° (MeOH, c=1.02, 23° C.).

No. 2a-105

CDCl₃ 300 MHz

93(1H, d, J=9.9 Hz), 1.09 and 1.21(each 3H, each s), 1.51-2.44(14H, m), 3.90(6H, s), 4.20(1H, m), 5.38-5.50(2H, m), 5.87(1H, d, J=9.0 Hz), 6.25 and 7.54 (each 1H, each d, J=15.6 Hz), 6.84(1H, d, J=8.1 Hz), 7.03(1H, d, J=1.8 Hz), 7.09(1H, dd, J=1.8 and 8.1 Hz).

IR(CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.

[α]_(D)=+77.3° (MeOH, c=1.01, 23° C.).

No. 2a-106

[α]_(D)=+67.0° (MeOH, c=1.00, 25° C.).

No. 2a-107

[α]_(D)=+66.6° (MeOH, c=1.01, 24° C.).

m.p. 168.0-170.0° C.

No. 2a-108

[α]_(D)=+61.8° (MeOH, c=1.00, 22° C.).

No. 2a-109

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.10 and 1.22(each 3H, each s), 1.51-2.45(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.21(1H, d, J=8.7 Hz), 7.25 and 7.60(each 2H, each d, J=8.7 Hz), 7.33-7.41(5H, s).

IR(CHCl₃): 3453, 3062, 3028, 3014, 2925, 2870, 1739, 1708, 1651, 1594, 1557, 1515, 1481/cm.

[α]_(D)=+61.0° (MeOH, c=1.01, 22° C.).

No. 2a- 110

CD₃OD 300 MHz

0.94(1H, d, J=9.9 Hz), 1.13 and 1.22(each 3H, each s), 1.54-2.37(14H, m), 4.12(1H, m), 5.38-5.49(2H, m), 7.25 and 7.68(each 2H, each d, J=8.7 Hz), 7.41(5H, s).

IR(KBr): 3435, 3058, 2986, 2920, 2866, 1635, 1595, 1562, 1521, 1482, 1439, 1411/cm.

[α]_(D)=+47.3° (MeOH, c=1.01, 23° C.).

No. 2a-111

[α]_(D)=+65.6° (MeOH, c=1.01, 24° C.).

No. 2a-112

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.51-2.46(14H, m), 4.27(1H, m), 5.35-5.50(2H, m), 6.22(1H, d, J=8.4 Hz), 7.40 and 7.66(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.

[α]_(D)=+65.6° (MeOH, c=1.01, 22° C.).

No. 2a-113

[α]_(D)=+59.6° (MeOH, c=1.00, 24° C.).

No. 2a-114

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.12 and 1.24(each 3H, each s), 1.52-2.46(14H, m), 4.29(1H, m), 5.35-5.51(2H, m), 6.28(1H, d, J=8.4 Hz), 7.70 and 7.83(each 2H, each d, J=8.4 Hz).

IR(CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.

[α]_(D)=+60.6° (MeOH, c=1.01, 22° C.).

No. 2a-115

[α]_(D)=+59.7° (MeOH, c=0.99, 24° C.).

No. 2a-116

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.39(3H, s), 4.27(1H, m), 5.33-5.51(2H, m), 6.24(1H, d, J=9.0 Hz), 7.23 and 7.62 (each 2H, each d, J=8.4 Hz). IR(CHCl₃): 3439, 3028, 3012, 2937, 2871, 2841, 1739, 1708, 1661, 1620, 1600, 1513/cm.

[α]_(D)=+59.7° (MeOH, c=0.99, 24° C.).

No. 2a-117

[α]_(D)=+56.7° (MeOH, c=1.00, 23° C.).

No. 2a-118

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.44(14H, m), 4.23(1H, m), 5.34-5.51(2H, m), 6.02(2H, s), 6.13(1H, d, J=8.7 Hz), 6.83(1H, dd, J=1.2 and 7.8 Hz), 7.22-7.25(2H, m).

IR(CHCl₃): 3453, 3031, 3020, 3012, 2924, 2870, 1740, 1708, 1650, 1619, 1605, 1519, 1504, 1480/cm.

[α]_(D)=+57.2° (MeOH, c=1.02, 23° C.).

No. 2a-119

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.07 and 1.23(each 3H, each s), 1.51-2.44(14H, m), 2.32(3H, s), 4.26(1H, m), 5.37-5.52(2H, m), 6.40(1H, d, J=9.0 Hz), 7.09(1H, m), 7.30(1H, m), 7.46(1H, m), 7.66(1H, m).

IR(CHCl₃): 3443, 3028, 3012, 2925, 2870, 1766, 1747, 1709, 1657, 1607, 1516, 1479/cm.

[α]_(D)=+53.2° (MeOH, c=0.99, 21° C.).

No. 2a-120

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.53-2.44(14H, m), 4.30(1H, m), 5.35-5.52(2H, m), 6.42(1H, d, J=8.7 Hz), 6.85(1H, m), 6.99(1H, dd, J=1.2 and 8.4 Hz), 7.27(1H, m), 7.39(1H, m).

IR(CHCl₃): 3463, 3033, 3021, 3014, 2992, 2924, 2870, 1708, 1643, 1597, 1523, 1488/cm.

[α]_(D)=+46.3° (MeOH, c=1.01, 21° C.).

No. 2a-121

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.47-2.47(14H, m), 3.95(3H, s), 4.31(1H, m), 5.32-5.50(2H, m), 6.98(1H, dd, J=0.9 and 8.4 Hz),7.09(1H, ddd, J=0.9, 7.7 and 8.4 Hz), 7.45(1H, m), 8.19(1H, dd, J=2.1 and 8.1 Hz), 8.32(1H, d, J=9.0 Hz).

IR(CHCl₃): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.

[α]_(D)=+38.1° (MeOH, c=1.02, 23° C.).

No. 2a-122

[α]_(D)=+42.3° (MeOH, c=0.99, 23° C.).

No. 2a-123

[α]_(D)=+38.7° (MeOH, c=1.00, 21° C.).

No. 2a-124

[α]_(D)=+45.0° (MeOH, c=1.01, 21° C.).

m.p. 119.0-120.0° C.

No. 2a- 125

[α]_(D)=+49.8° (MeOH, c=1.01, 22° C.).

No. 2a- 126

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.47(14H, m), 4.266(1H, m), 5.34-5.50(2H, m), 6.22(1H, d, J=8.7 Hz), 7.55-7.61(4H, m).

IR(CHCl₃): 3400, 3078, 3028, 3020, 3007, 2924, 2870, 2842, 1736, 1708, 1640, 1600, 1536, 1483, 1470/cm.

[α]_(D)=+63.0° (MeOH, c=1.01, 23° C.).

No. 2a-127

CDCl₃ 300 MHz

0.91(1H, d, J=10.2 Hz), 1.10 and 1.20(each 3H, each s), 1.50-2.42(14H, m), 4.23(1H, m), 5.31-5.51(2H, m), 6.45(1H, d, J=8.4 Hz), 7.01(1H, t, J=7.4 Hz), 7.22-7.27(2H, m), 7.33-7.40(4H, m), 7.53(2H, d, J=9.0 Hz), 8.30 and 8.48(each 1H, each s).

IR(CHCl₃): 3452, 3028, 3022, 3015, 2925, 2870, 1708, 1654, 1590, 1514, 1478/cm.

[α]_(D)=+59.5° (MeOH, c=1.01, 23° C.).

No. 2a-128

d₆-DMSO 300 MHz

0.84(1H, d, J=9.9 Hz), 1.06 and 1.19(each 3H, each s), 1.37-2.37(14H, m), 3.79(1H, m), 5.35-5.51(2H, m), 6.08(1H, d, J=8.7 Hz), 6.85-6.90(1H, m), 7.18-7.23(2H, m), 7.35-7.38(2H, m), 8.42(1H, s), 12.00(1H, s).

IR(Nujol): 3395, 3345, 2925, 2866, 2623, 2506, 1697, 1658, 1638, 1597, 1557/cm.

[α]_(D)=+26.0° (MeOH, c=1.01, 23° C.).

m.p. 164.0-166.0° C.

No. 2a-129

CDCl₃ 300 MHz

1.01(1H, d, J=10.0 Hz), 1.17 and 1.25(each 3H, each s), 1.54-2.52(14H, m), 4.34(1H, m), 5.36-5.57(2H, m), 6.42(1H, d, J=8.6 Hz), 7.51-7.60(2H, m), 7.77(1H, dd J=1.8 and 8.6 Hz), 7.85-7.96(3H, m), 8.24(1H, brs).

IR(CHCl₃): 3451, 3060, 3028, 3010, 2925, 2870, 1708, 1652, 1629, 1600, 1517, 1502/cm.

[α]_(D)=+68.6° (MeOH, c=1.00, 22° C.).

No. 2a-130

CDCl₃ 300 MHz

1.02(1H, d, J=10.2 Hz), 1.04 and 1.26(each 3H, each s), 1.54-2.52(14H, m), 4.41(1H, m), 5.41-5.58(2H, m), 6.14(1H, d, J=9.0 Hz), 7.43-7.59(4H, m), 7.85-7.92(2H, m), 8.27(1H, dd, J=1.8 and 7.2 Hz).

IR(CHCl₃): 3436, 3032, 3010, 2924, 2870, 2664, 1708, 1652, 1512, 1498/cm.

[α]_(D)=+93.9° (MeOH, c=1.00, 22° C.)

m.p. 94.0-96.0° C.

No. 2a-131

[α]_(D)=+50.2° (MeOH, c=0.95, 21° C.).

No. 2a-132

[α]_(D)=+10.9° (MeOH, c=0.92, 21° C.).

No. 2a-133

[α]_(D)=+60.4° (MeOH, c=1.00, 21° C.).

No. 2a- 134

[α]_(D)=+38.5° (MeOH, c=1.01, 23° C.).

No. 2a-135

[α]_(D)=+52.5° (MeOH, c=1.01, 23° C.).

m.p. 180.0-182.0° C.

No. 2a-136

[α]_(D)=+35.3° (MeOH, c=1.02, 23° C.).

m.p. 79.0-80.0° C.

No. 2a-137

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.43(3H, t, J=6.9 Hz), 1.52-2.44(14H, m), 4.03(2H, q, J=6.9 Hz), 4.26(1H, m), 5.33-5.50(2H, m), 6.19(1H, d, J=8.7 Hz), 6.88-7.00(6H, m), 7.65-7.68(2H, m).

IR(CHCl₃): 3455, 3031, 3024, 3014, 2988, 2925, 2870, 1741, 1708, 1649, 1602, 1521, 1504, 1490/cm.

[α]_(D)=+52.0° (MeOH, c=1.01, 23° C.).

No. 2a-138

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.35(6H, d, J=6.0 Hz), 1.53-2.46(14H, m), 4.25(1H, m), 4.51(1H, m), 5.33-5.50(2H,m),6.12(1H, d, J=9.0 Hz), 6.87-6.99(6H, m), 7.65-7.68(2H, m).

IR(CHCl₃): 3454, 3031, 3014, 2980, 2925, 2870, 1741, 1708, 1649, 1602, 1 522, 1490/cm.

[α]_(D)=+50.0° (MeOH, c=1.05, 22° C.).

No. 2a-139

CDCl₃ 300 MHz

1.00(1H, d, J=10.2 Hz), 1.16 and 1.24(each 3H, each s), 1.59-2.52(14H, m), 4.31(1H, m), 5.40-5.53(2H, m),6.36(1H, d, J=8.7 Hz), 6.70(1H, d, J=1.5 Hz), 7.12(1H, m), 7.30(1H, m), 7.47(1H, dd, J=0.6 and 8.1 Hz), 7.61(1H, d, J=8.4 Hz).

IR(CHCl₃): 3449, 3243, 3029, 3022, 3013, 2925, 2871, 1707, 1631, 1542, 1505/cm.

[α]_(D)=+63.4° (MeOH, c=1.00, 23° C.).

m.p. 178.0-179.0° C.

No. 2a-140

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.18 and 1.23(each 3H, each s), 1.57-2.50(14H, m), 4.35(1H, m), 5.32-5.55(2H, m), 6.42(1H, d, J=8.7 Hz), 6.70(1H, d, J=1.5 Hz), 7.21-7.24(2H, m), 7.46(1H, m), 7.76(1H, m), 7.86(1H, d, J=3.0 Hz), 10.20(1H, s).

IR(CHCl₃): 3465, 3010, 2924, 1739, 1604, 1546, 1504/cm.

[α]_(D)=+39.4° (MeOH, c=1.01, 22° C.).

m.p. 167.0-168.0° C.

No. 2a-141

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.55-2.44(14H, m), 3.84(3H, s), 4.27(1H, m), 5.34-5.52(2H, m), 6.28(1H, d, J=9.0 Hz), 6.91 and 7.47 (each 2H, each d, J=9.0 Hz), 6.98 and 7.14(each 1H, each d, J=16.5 Hz), 7.54 and 7.70(each 2H, eachd, J=8.7 Hz).

IR(CHCl₃): 3453, 3025, 3015, 2925, 2870, 2839, 1740, 1708, 1649, 1602, 1510, 1493, 1470/cm.

[α]_(D)=+73.4° (MeOH, c=1.02, 22° C.).

m.p. 155.0-157.0° C.

No. 2a-142

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.45(14H, m), 3.79(3H, s), 4.27(1H, m), 5.34-5.50(2H, m), 6.24(1H, d, J=9.0 Hz), 6.49 and 6.62(each 1H each d, J=12.3 Hz), 6.77 and 7.16(each 2H, each d, J=8.7 Hz), 7.32 and 7.59(each 2H, each, d, J=8.1 Hz).

IR(CHCl₃): 3453, 3025, 3014, 2925, 2870, 2839, 1739, 1708, 1649, 1606, 1510, 1494/cm.

[α]_(D)=+60.7° (MeOH, c=0.99, 22° C.).

No. 2a-143

[α]_(D)=+57.3° (MeOH, c=1.01, 23° C.).

No. 2a-144

[α]_(D)=+12.2° (MeOH, c=1.00, 23° C.).

m.p. 114.0-116.0° C.

No. 2a-145

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.10 and 1.21(each 3H, each s), 1.52-2.44(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.37(1H, d, J=8.7 Hz), 7.45-7.47(3H, m), 7.62-7.66(2H, m), 7.69 and 7.80(each 2H, each d, J=7.5 Hz, ).

IR(CHCl₃): 3449, 3058, 3027, 3012, 2925, 2870, 1708, 1655, 1513, 1481, 1043/cm.

[α]_(D)=+61.0° (MeOH, c=1.01, 23° C.).

No. 2a-146

CDCl₃ 300 MHz

0.95(1H, d, J=10.5 Hz), 1.09 and 1.21(each 3H, each s), 1.50-2.41(14H, m), 4.25(1H, m), 5.33-5.49(2H, m), 6.33(1H, d, J=8.4 Hz), 7.49-7.61(3H, m), 7.91-7.92(2H, m), 7.82 and 7.97(each 2H, each d, J=8.7 Hz, ).

IR(CHCl₃): 3447, 3029, 3023, 3015, 2925, 2870, 1708, 1660, 1514, 1484, 1321, 1161/cm.

[α]_(D)=+62.0° (MeOH, c=1.00, 22° C.).

No. 2a-147

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.51(3H, s), 4.26(1H, m), 5.34-5.51(2H, m), 6.23(1H, d, J=8.4 Hz), 7.26 and 7.64 (each 2H, each d, J=8.4 Hz).

IR(CHCl₃): 3453, 3027, 3015, 2925, 2870, 2665, 1708, 1648, 1596, 1516, 1484/cm.

[α]_(D)=+67.7° (MeOH, c=0.82, 22° C.).

No. 2a-148

[α]_(D)=+72.5° (MeOH, c=1.01, 25° C.).

No. 2a-149

[α]_(D)=+67.8° (MeOH, c=0.98, 25° C.).

No. 2a-150

CDCl₃ 300 MHz

0.94(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.22(1H, m), 5.36-5.55(2H, m), 6.48(1H, d, J=8.4 Hz), 8.35(1H, s), 8.90(1H, s).

IR(CHCl₃): 3443, 3374, 3091, 3024, 3012, 2925, 2871, 1709, 1652, 1525, 1494/cm.

[α]_(D)=+58.1° (MeOH, c=1.01, 23° C.).

m.p. 120.0-122.0° C.

No. 2a-151

[α]_(D)=+40.6° (MeOH, c=1.01, 23° C.).

No. 2a-152

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.10 and 1.24(each 3H, each s), 1.50-2.50(14H, m), 2.71(3H, s), 4.26(1H, m), 5.37-5.51(2H, m), 6.02(1H, d, J=9.0 Hz), 8.73(1H, s).

IR(CHCl₃): 3463, 3435, 3087, 3025, 3014, 2925, 2870, 1708, 1649, 1523, 1503/cm.

[α]_(D)=+54.1° (MeOH, c=1.02, 22° C.).

No. 2a-153

CDCl₃ 300 MHz

0.95(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.50(14H, m), 2.50(3H, s), 4.26(1H, m), 5.36-5.51(2H, m), 6.01(1H, d, J=8.4 Hz), 6.88(1H, d, J=5.1 Hz), 7.26(1H, d, J=5.1 Hz).

IR(CHCl₃): 3469, 3431, 3025, 3013, 2925, 2871, 2664, 1708, 1639, 1544, 1505/cm.

[α]_(D)=+35.8° (MeOH, c=1.03, 22° C.).

No. 2a-154

CDCl₃ 300 MHz

0.95(1H, d, J=9.9 Hz), 1.10 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 2.51(3H, d, J=1.2 Hz), 4.26(1H, m), 5.34-5.50(2H, m), 6.00(1H, d, J=8.4 Hz), 6.73(1H, dd, J=5.1 and 3.6 Hz), 7.29(1H, d, J=3.6 Hz).

IR(CHCl₃): 3450, 3431, 3026, 3011, 2925, 2869, 1739, 1708, 1639, 1547, 1508/cm.

[α]_(D)=+50.5° (MeOH, c=1.01, 22° C.).

No. 2a-155

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.19 and 1.25(each 3H, each s), 1.53-2.48(14H, m), 4.31(1H, m), 5.36-5.51(2H, m), 6.79(1H, d, J=9.3 Hz), 7.29(1H, m), 7.41(1H, m), 7.48(1H, s), 7.51(1H, m), 7.66(1H, d, J=8.1 Hz).

IR(CHCl₃): 3436, 3029, 3024, 3015, 2925, 2871, 2670, 1708, 1659, 1598, 1510/cm.

[α]_(D)=+69.1° (MeOH, c=1.01, 22° C.).

No. 2a-156

CDCl₃: CD₃O_(D)=10:1 300 MHz

0.99(1H, d, J=9.9 Hz), 1.11 and 1.21(each 3H, each s), 1.56-2.58(14H, m), 4.22(1H, m), 5.35-5.59(2H, m), 6.83(1H, d, J=8.4 Hz),7.48(1H, d, J=8.4 Hz), 7.61(1H, dd, J=1.5 and 8.4 Hz), 8.09(1H, d, J=1.5 Hz), 8.12(1H, s).

IR(KBr): 3422, 3115, 2985, 2922, 2869, 2609, 1708, 1636, 1578, 1529, 1470/cm.

[α]_(D)=+62.8° (MeOH, c=1.01, 22° C.).

No. 2a-157

[α]_(D)=+40.0° (MeOH, c=0.95, 22° C.).

No. 2a-158

CDCl₃ 300 MHz

1.00(1H, d, J=10.5 Hz), 1.17 and 1.24(each 3H, each s), 1.54-2.50(14H, m), 4.34(1H, m), 5.36-5.52(2H, m), 7.80(1H, d, J=9.0 Hz), 9.30(1H, s).

IR(CHCl₃): 3410, 3122, 3030, 3012, 2925, 2871, 2668, 1709, 1667, 1538, 1466/cm.

[α]_(D)=+44.9° (MeOH, c=0.99, 22° C.).

No. 2a-159

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.13 and 1.22(each 3H, each s), 1.55-2.43(14H, m), 3.03(6H, s), 4.23(1H, m), 5.32-5.51(2H, m), 6.16(1H, d, J=8.7 Hz),6.87 and 7.63 (each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3457, 3028, 3006, 2924, 2870, 2654, 1739, 1709, 1637, 1608, 1608, 1534, 1501/cm.

[α]_(D)=+64.8° (MeOH, c=1.01, 22° C.).

No. 2a-160

d₆-DMSO 300 MHz

0.83(1H, d, J=9.9 Hz), 1.02 and 1.19(each 3H, each s), 1.38-1.61(3H, m), 1.90-2.32(11H, m), 3.90(1H, m), 5.41-5.44(2H, m), 7.32(1H, dd, J=.09 and 7.2 Hz), 7.45-7.60(2H, m), 7.77(1H, dd, J=0.9 and 7.8 Hz), 8.03(1H, d, J=6.9 Hz), 12.40(1H, s).

IR(Nujol): 3315, 2924, 2856, 2656, 2535, 1737, 1703, 1637, 1598, 1581, 1541/cm.

[α]_(D)=+78.5° (MeOH, c=1.01, 24° C.).

m.p. 161.0-162.0° C.

No. 2a-161

[α]_(D)=+65.3° (MeOH, c=1.00, 22° C.).

No. 2a-162

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.13 and 1.25(each 3H, each s), 1.53-2.45(14H, m), 4.30(1H, m), 5.36-5.51(2H, m), 6.32(1H, d, J=8.4 Hz), 7.88 and 8.28(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3448, 3029, 3016, 2925, 2870, 1708, 1664, 1602, 1527, 1484, 1347/cm.

[α]_(D)=+72.7° (MeOH, c=1.02, 22° C.).

No. 2a-163

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.55-2.51(14H, m), 4.26(1H, m), 5.36-5.57(2H, m), 6.68(1H, d, J=7.8 Hz), 7.41(1H, dd, J=4.8 and 8.1 Hz), 8.20(1H, d, J=8.1 Hz), 8.66(1H, d, J=4.8 Hz), 9.00(1H, s).

IR(CHCl₃): 3448, 3026, 3013, 2925, 2870, 2534, 1709, 1658, 1590, 1515, 1471/cm.

[α]_(D)=+71.3° (MeOH, c=1.01, 22° C.).

No. 2a-164

[α]_(D)=+40.8° (MeOH, c=0.98, 22° C.).

No. 2a-165

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.11 and 1.24(each 3H, each s), 1.55-2.52(14H, m), 4.24(1H, m), 5.37-5.57(2H, m), 6.63(1H, d, J=7.8 Hz), 7.59 and 8.63(each 2H each d, J=6.0 Hz).

IR(CHCl₃): 3447, 3346, 3028, 3016, 2925, 2870, 2538, 1941, 1708, 1662, 1556, 1516/cm.

[α]_(D)=+75.4° (MeOH, c=1.01, 22° C.).

No. 2a-166

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.51-2.44(14H, m), 2.95(6H, s), 4.25(1H, m), 5.33-5.50(2H, m), 6.19(1H, d, J=8.7 Hz), 6.77 and 6.97(each 2H, each d, J=8.4 Hz), 6.94 and 7.65(each 2H, each d, J=9.0 Hz).

IR(CHCl₃): 3453, 3024, 3016, 2924, 2871, 2806, 1739, 1708, 1647, 1612, 1604, 1515, 1490/cm.

[α]_(D)=+53.1° (MeOH, c=1.02, 23° C.).

m.p. 104.0-105.5° C.

No. 2a-167

CDCl₃ 300 MHz

1.01(1H, d, J=9.9 Hz), 1.19 and 1.26(each 3H, each s), 1.56-2.53(14H, m), 4.37(1H, m), 5.35-5.55(2H, m), 6.47(1H, d, J=8.4 Hz), 7.61-7.71(2H, m), 7.79(2H, s), 7.89-7.97(2H, m), 8.27(1H, d, J=2.1 Hz), 8.66-8.73(2H, m).

IR(CHCl₃): 3450, 3024, 3014, 2925, 2870, 2667, 1707, 1650, 1531, 1509/cm.

[α]_(D)=+70.5° (MeOH, c=1.00, 22° C.).

No. 2a-168

CDCl₃ 300 MHz

1.02(1H, d, J=10.2 Hz), 1.20 and 1.26(each 3H, each s), 1.56-2.50(14H, m), 4.38(1H, m), 5.36-5.56(2H, m), 6.51(1H, d, J=8.4 Hz), 7.61-7.93(7H, m), 8.74(1H, d, J=8.4 Hz), 9.15(1H, s).

IR(CHCl₃): 3517, 3451, 3060, 3028, 3011, 2925, 2870, 2664, 1709, 1651, 1519, 1498/cm.

[α]_(D)=+54.4° (MeOH, c=1.00, 23° C.).

No. 2a-169

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.09 and 1.21(each 3H, each s), 1.50-2.44(14H, m), 3.85(3H, s), 4.24(1H, m), 5.32-5.48(2H, m), 6.19(1H, d, J=8.4 Hz), 6.94 and 7.45(each 2H, each d, J=9.0 Hz), 7.11 and 7.45(each 2H, each d, J=8.7 Hz).

IR(CHCl₃): 3516, 3453, 3029, 3009, 2925, 2870, 2840, 2665, 1708, 1650, 1593, 1515, 1493, 1482/cm.

[α]_(D)=+57.8° (MeOH, c=1.00, 23° C.).

No. 2a-170

CDCl₃ 300 MHz

0.98(1H, d, J=10.2 Hz), 1.15 and 1.24(each 3H, each s), 1.52-2.50(14H, m), 4.28(1H, m), 5.33-5.54(2H, m), 6.25(1H, d, J=8.2 Hz), 7.38-7.44(2H, m), 7.74(1H, s), 7.81-7.86(2H, m).

IR(CHCl₃): 3517, 3448, 3427, 3024, 3013, 2925, 2870, 2669, 1708, 1650, 1562, 1535, 1500/cm.

[α]_(D)=+61.6° (MeOH, c=1.00, 23° C.).

No. 2a-171

CDCl₃ 300 MHz 0.96(1H, d, J=10.2 Hz, 1.11 and 1.22(each 3H, each s), 1.52-2.42(14H, m), 2.48 (3H, s), 4.21(1H, m), 5.31-5.52(2H, m), 6.06(1H, d, J=8.2 Hz),6.97 and 7.59(each 1H, each d, J=1.2 Hz).

IR(CHCl₃): 3452, 3113, 3028, 3007, 2925, 2870, 2669, 1708, 1645, 1554, 1509/cm.

[α]_(D)=+52.4° (MeOH, c=1.00, 23° C.).

No. 2a-172

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.09 and 1.28(each 3H, each s), 1.50-2.40(14H, m), 2.69(3H, s), 4.24(1H, m), 5.35-5.51(2H, m), 5.96(1H, d, J=8.7 Hz),7.03 and 7.07 (each 1H, each d, J=5.4 Hz).

IR(CHCl₃): 3451, 3031, 3013, 2925, 2870, 2666, 1708, 1647, 1542, 1497/cm.

[α]_(D)=+51.20 (MeOH, c=1.00, 23° C.).

No. 2a-173

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.10 and 1.23(each 3H, each s), 1.50-2.45(14H, m), 4.22(1H, m), 5.35-5.49(2H, m), 6.05(1H, d, J=8.4 Hz), 7.26 and 7.75(each 1H, each d, J=1.5 Hz).

IR(CHCl₃): 3451, 3011, 3029, 3011, 2925, 2870, 1708, 1652, 1538, 1500/cm.

[α]_(D)=+50.6° (MeOH, c=1.01, 23° C.).

No. 2a-174

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.13 and 1.23(each 3H, each s), 1.52-2.50(14H, m), 4.29(1H, m), 5.35-5.51(2H, m), 7.02(1H, d, J=8.4 Hz), 7.32 and 8.16(each 1H, each d, J=3.9 Hz).

IR(CHCl₃): 3417, 3115, 3023, 3014, 2925, 2870, 1708, 1645, 1530/cm.

[α]_(D)=+48.8° (MeOH, c=1.02, 23° C.).

No. 2a-175

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.50-2.52(14H, m), 2.52(3H, s), 4.29(1H, m), 5.34-5.51(2H, m), 7.78(1H, d, J=9.0 Hz), 7.24 and 7.52 (each 1H, each d, J=5.4 Hz).

IR(CHCl₃): 3329, 3093, 3023, 3015, 2924, 2871, 1708, 1640, 1526/cm.

[α]_(D)=+45.0° (MeOH, c=1.01, 23° C.).

No. 2a-176

CDCl₃ 300 MHz

0.95(1H, d, J=10.5 Hz), 1.09 and 1.23(each 3H, each s), 1.52-2.46(14H, m), 2.40(3H, d, J=0.9 Hz), 4.24(1H, m), 5.35-5.51(2H, m), 6.05(1H, d, J=8.7 Hz), 6.95(1H, m), 7.57(1H, d, J=3.3 Hz).

IR(CHCl₃): 3517, 3444, 3103, 3024, 3013, 2926, 2870, 1739, 1708, 1649, 1636, 1507/cm.

[α]_(D)=+54.8° (MeOH, c=1.01, 23° C.).

m.p. 97.0-99.0° C.

No. 2a-177

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.52-2.45(14H, m), 3.93(3H, s), 4.27(1H, m), 5.34-5.50(2H, m), 6, 35(1H, d, J=3.3 Hz), 7.80(1H, d, J=8.7 Hz), 8.10(1H, d, J=3.3 Hz).

IR(CHCl₃): 3395, 3121, 3031, 3019, 3012, 2925, 2871, 1739, 1709, 1640, 1557, 1533/cm.

[α]_(D)=+22.8° (MeOH, c=1.01, 23° C.).

m.p. 109.0-112.0° C.

No. 2a-178

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.10 and 1.23(each 3H, each s), 1.51-2.45(14H, m), 4.24(1H, m), 5.36-5.50(2H, m), 6.09(1H, d, J=8.4 Hz), 7.17-7.31(6H, m), 7.95(1H, d, J=1.5 Hz).

IR(CHCl₈): 3510, 3451, 3062, 3031, 3022, 3011, 2925, 2870, 2662, 1708, 1651, 1582, 1535, 1497, 1477/cm.

[α]_(D=+47.9)° (MeOH, c=1.01, 25° C.).

No. 2a-179

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.52-2.48(14H, m), 4.30(1H, m), 5.36-5.52(2H, m), 6.73(1H, d, J=9.0 Hz), 6.26 and 7.37(each 1H, each d, J=6.0 Hz).

IR(CHCl₃): 3509, 3429, 3115, 3094, 3025, 3014, 2925, 2871, 2666, 1708, 1649, 1529, 1510/cm.

[α]_(D)=+51.0° (MeOH, c=1.02, 25° C.).

No. 2a-180

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.14 and 1.24(each 3H, each s), 1.52-2.46(14H, m), 3.89(3H, s), 4.21(1H, m), 5.35-5.50(2H, m), 6.05(1H, d, J=8.4 Hz), 6.46 and 7.04 (each 1H, each d, J=1.8 Hz).

IR(CHCl₃): 3516, 3450, 3114, 3031, 3010, 2925, 2871, 1708, 1648, 1546, 1511, 1477/cm.

[α]_(D)=+49.1° (MeOH, c=1.01, 25° C.).

No. 2a-181

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.14 and 1.23(each 3H, each s), 1.52-2.48(14H, m), 2.42(3H, s), 4.31(1H, m), 5.34-5.52(2H, m), 8.07(1H, d, J=9.3 Hz), 7.27 and 8.17 (each 1H, each d, J=3.3 Hz).

IR(CHCl₃): 3510, 3301, 3112, 3023, 3007, 2924, 2871, 2663, 1708, 1636, 1534/cm.

[α]_(D)=+41.0° (MeOH, c=0.96, 25° C.).

No. 2a-182

CDCl₃ 300 MHz 0.96(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.46(14H, m), 2.51

(3H, s), 4.21(1H, m), 5.35-5.51(2H, m), 6.05(1H, d, J=8.1 Hz), 7.26 and 7.78 (each 1H, each d, J=1.8 Hz).

IR(CHCl₃): 3509, 3450, 3109, 3024, 3012, 2925, 2870, 2666, 1708, 1650, 1535, 1498, 1471/cm.

[α]_(D)=+52.9° (MeOH, c=0.95, 25° C.).

No. 2a-183

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.12 and 1.22(each 3H, each s), 1.52-2.46(14H, m), 4.25(1H, m), 5.33-5.51(2H, m), 6.17(1H, d, J=8.7 Hz), 7.01-7.05(3H, m).7.14 and 7.62(each 2H, each d, J=8.7 Hz), 7.27-7.34(2H, m).

IR(CHCl₃): 3428, 3026, 3015, 2925, 2870, 2666, 1739, 1708, 1643, 1613, 1594, 1526, 1499/cm.

[α]_(D)=+64.8° (MeOH, c=1.02, 23° C.).

No. 2a-184

CDCl₃ 300 MHz

1.01(1H, d, J=10.2 Hz), 1.18 and 1.26(each 3H, each s), 1.55-2.50(14H, m), 4.35(1H, m), 5.35-5.55(2H, m), 6.42(1H, d, J=8.7 Hz), 7.46-7.52(2H, m).7.73(1H, dd, J=1.8 and 8.4 Hz), 7.83-7.89(2H, m), 8.21(1H, m), 8.59(1H, d, J=1.5 Hz).

IR(CHCl₃): 3451, 3031, 3014, 2925, 2870, 2660, 1739, 1708, 1650, 1604, 1513, 1463/cm.

[α]_(D)=+58.3° (MeOH, c=1.00, 23° C.).

No. 2a-185

CDCl₃ 300 MHz

1.00(1H, d, J=10.2 Hz), 1.18 and 1.25(each 3H, each s), 1.55-2.50(14H, m), 4.34(1H, m), 5.35-5.54(2H, m), 6.36(1H, d, J=8.7 Hz), 7.37(1H, t, J=7.4 Hz), 7.50(1H, m), 7.57-7.59(2H, m), 7.79(1H, dd, J=1.8 and 8.1 Hz), 7.99(1H, d, J=7.8 Hz), 8.39(1H, d, J=1.8 Hz).

IR(CHCl₃): 3451, 3030, 3020, 2870, 2665, 1708, 1652, 1632, 1603, 1586, 1514, 1469, 1448/cm.

[α]_(D)=+59.4° (MeOH, c=1.01, 24° C.).

No. 2a-186

CDCl₃ 300 MHz

1.00(1H, d, J=10.5 Hz), 1.17 and 1.25(each 3H, each s), 1.54-2.50(14H, m), 4.33(1H, m), 5.35-5.54(2H, m), 6.37(1H, d, J=8.7 Hz), 7.37(1H, t, J=7.4 Hz), 7.51(1H, t, J=7.8 Hz), 7.56(1H, m), 7.70(1H, dd, J=1.2 and 8.4 Hz), 7.97(3H, m).

IR(CHCl₃): 3451, 3030, 3014, 2924, 2870, 2671, 1739, 1708, 1652, 1577, 1517, 1488, 1471/cm.

[α]_(D)=+72.2° (MeOH, c=1.00, 24° C.).

No. 2a-187

CDCl₃ 300 MHz

1.00(1H, d, J=9.8 Hz), 1.18 and 1.25(each 3H, each s), 1.54-2.53(14H, m), 4.07(3H, s), 4.37(1H, m), 5.30-5.54(2H, m), 7.34(1H, m), 7.47(1H, s), 7.47-7.60(2H, m), 7.93(1H, d, J=7.8 Hz), 8.43(1H, s), 8.49(1H, d, J=9.0 Hz).

IR(CHCl₃): 3397, 3074, 3027, 3020, 3009, 2924, 1738, 1708, 1647, 1633, 1534, 1465, 1453/cm.

[α]_(D)=+43.7° (MeOH, c=1.01, 25° C.).

No. 2a-188

CDCl₃ 300 MHz

0.97(1H, d, J=10.2 Hz), 1.11 and 1.23(each 3H, each s), 1.53-2.50(14H, m), 4.23(1H, m), 5.37-5.50(2H, m), 6.10(1H, d, J=9.0 Hz), 6.20(1H, m), 6.51(1H, m), 6.97(1H, m), 10.81 (1H, brs).

IR(CHCl₃): 3450, 3236, 3112, 3029, 3015, 2925, 2871, 2645, 1701, 1616, 1558, 1516/cm.

[α]_(D)=+50.6° (MeOH, c=1.01, 24° C.).

No. 2a-189

CDCl₃ 300 MHz

0.94(1H, d, J=9.9 Hz), 1.11 and 1.23(each 3H, each s), 1.50-2.46(14H, m), 3.93(3H, s), 4.18(1H, m),5.35-5.52(2H, m), 6.03(1H, d, J=9.3 Hz), 6.09(1H, m), 6.48m), 6.73(1H, m).

IR(CHCl₃): 3452, 3102, 3028, 3007, 2925, 2871, 2666, 1739, 1708, 1650, 1536, 1499, 1471/cm.

[α]_(D)=+49.8° (MeOH, c=1.01, 23° C.).

m.p. 101.5-103.5° C.

No. 2a-190

CDCl₃ 300 MHz

0.94(1H, d, J=10.2 Hz), 1.11 and 1.21(each 3H, each s), 1.54-2.47(14H, m), 4.23(1H, m), 5.33-5.52(2H, m), 6.06(1H, d, J=9.0 Hz), 6.34(1H, m), 6.75(1H, m), 6.36(1H, m), 9.71(1H, brs).

IR(CHCl₃): 3470, 3215, 3030, 3020, 3010, 2925, 2871, 2664, 1709, 1613, 1564, 1510/ cm.

[α]_(D)=+43.3° (MeOH, c=1.01, 24° C.).

No. 2a-191

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.55-2.44(14H, m), 3.66(3H, s), 4.20(1H, m), 5.35-5.51(2H, m), 5.93(1H, d, J=8.4 Hz), 6.27(1H, dd, J=1.8 and 2.7 Hz), 6.56(1H, t, J=2.7 Hz), 7.19(1H, t, J=1.8 Hz).

IR(CHCl₃): 3452, 3031, 3018, 3006, 2925, 2871, 2662, 1736, 1710, 1634, 1609, 1556, 1498/cm.

[α]_(D)=+43.1° (MeOH, c=1.01, 23° C.).

No. 2a-192

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.11 and 1.21(each 3H, each s), 1.43(3H, t, J=7.5 Hz), 1.54-2.44(14H, m), 3.93(2H, q, J=7.5 Hz), 4.21(1H, m), 5.33-5.51(2H,m), 5.94(1H, d, J=8.4 Hz), 6.27(1H, dd, J=1.8 and 2.7 Hz), 6.62(1H, t, J=2.7 Hz), 7.26(1H, t, J=1.8 Hz).

IR(CHCl₃): 3630, 3452, 3032, 3018, 3006, 2925, 2871, 2661, 1735, 1710, 1633, 1610, 1555, 1497/cm.

[α]_(D)=+40.1° (MeOH, c=1.00, 23° C.).

No. 2a-193

CDCl₃ 300 MHz

0.95(1H, d, J=10.2 Hz), 1.10 and 1.22(each 3H, each s), 1.53-2.49(14H, m), 2.58(3H, s), 4.21(1H, m), 5.36-6.54(2H, m), 6.15(1H, d, J=8.1 Hz), 6.52(1H, dd, J=1.8 and 3.6 Hz), 7.29(1H, t, J=3.6 Hz), 7.94(1H, t, J=1.8 Hz).

IR(CHCl₃): 3516, 3450, 3410, 3152, 3027, 3015, 2925, 2871, 2670, 1732, 1648, 1574, 1509/cm.

[α]_(D)=+45.0° (MeOH, c=1.01, 25° C.).

No. 2a-194

CDCl₃ 300 MHz

0.99(1H, d, J=10.2 Hz), 1.11 and 1.24(each 3H, each s), 1.52-2.53(14H, m), 4.34(1H, m), 5.33-5.57(2H, m), 6.21(1H, d, J=8.6 Hz), 7.35-7.50(2H, m), 7.83(1H, s), 7.86(1H, m), .8.31(1H, m).

IR(CHCl₃): 3443, 3067, 3013, 2925, 2870, 2665, 1708, 1651, 1515, 1493/cm.

[α]_(D)=+55.7° (MeOH, c=1.01, 23° C.).

No. 2a-195

CDCl₃ 300 MHz

1.01(1H, d, J=10.0 Hz), 1.06 and 1.26(each 3H, each s), 1.50-2.64(14H, m), 2.68(3H, s), 4.40(1H, m), 5.36-5.61(2H, m), 6.02(1H, d, J=9.4 Hz), 7.30-7.42(2H, m), 7.73-7.86(2H, m).

IR(CHCl₃): 3510, 3434, 3062, 3029, 3014, 2924, 2871, 2669, 1708, 1650, 1563, 1539, 1500/cm.

[α]_(D)=+72.4° (MeOH, c=1.00, 23° C.).

m.p. 11 1.0-112.0° C.

No. 2a-196

CDCl₃ 300 MHz

0.42 and 1.04(each 3H, each s), 0.80(1H, d, J=10.0 Hz), 1.11-2.48(14H, m), 2.24(3H, s), 4.02(1H, m), 5.23-5.44(2H, m), 5.53(1H, d, J=8.8 Hz), 7.27-7.31(2H, m), 7.42-7.48(3H, m), 7.93(1H, s).

IR(CHCl₃): 3419, 3114, 3025, 3006, 2924, 2871, 2662, 1737, 1709, 1636, 1540, 1519/cm.

[α]_(D)=+43.7° (MeOH, c=1.01, 23° C.).

No. 2a-197

CDCl₃ 300 MHz

0.95(1H, d, J=10.0 Hz), 1.09 and 1.23(each 3H, each s), 1.54-2.46(18H, m), 2.77(4H, brs), 4.21(1H, m), 5.32-5.54(2H, m), 6.02(1H, d, J=8.6 Hz), 7.43(1H, s).

IR(CHCl₃): 3445, 3101, 3024, 3014, 2928, 2865, 2661, 1739, 1708 1646, 1550, 1507/cm.

[α]_(D)=+51.9° (MeOH, c=1.01, 23° C.).

No. 2a-198

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.50-2.44(14H, m), 4.24(1H, m), 4.42(2H, s), 5.35-5.49(2H, m), 6.25(1H, d, J=8.1 Hz), 7.33(1H,m),7.43(1H, dd, J=1.5and 7.5 Hz), 7.49(1H, d, J=8.1 Hz), 7.60-7.63(1H,m), 7.68(1H, dd, J=1.8 and 7.8 Hz), 8.02(1H, d, J=1.8 Hz), 8.19(1H, dd, J=1.5 and 8.1 Hz).

IR(CHCl₃): 3448, 3030, 3012, 2925, 2870, 1739, 1708, 1671, 1588, 1559, 1514, 1472/cm.

[α]_(D)=+56.9° (MeOH, c=1.01, 24° C.).

No. 2a-199

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.11 and 1.22(each 3H, each s), 1.51-2.46(14H, m), 3.40(1H, m), 3.76(1H, m), 4.24(1H, m), 5.33-5.51(3H, m), 6.25(1H, m), 7.16(1H, m), 7.24-7.33(2H, m), 7.46(1H, d, J=7.5 Hz), 7.52-7.60(2H, m), 7.85(1H, dd, J=1.8 and 4.5 Hz).

IR(CHCl₃): 3583, 3447, 3062, 3028, 3013, 2924, 2871, 2663, 1708, 1651, 1600, 1557, 1514, 1471/cm.

[α]_(D)=+54.8° (MeOH, c=1.00, 23° C.).

No. 2a-200

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.12 and 1.23(each 3H, each s), 1.51-2.46(14H, m), 4.25(1H, m), 5.34-5.51(2H, m), 6.25(1H, d, J=8.4 Hz), 7.02 and 7.10(each, 1H, each d, J=12.3 Hz), 7.23-7.33(4H, m), 7.50(1H, m), 7.64(1H, dd, J=1.8 and 7.8 Hz), 7.82(1H, d, J=1.8 Hz).

IR(CHCl₃): 3450, 3060, 3025, 3014, 2925, 2871, 2662, 1708, 1653, 1596, 1542, 1513, 1473/cm.

[α]_(D)=+62.5° (MeOH, c=1.00, 24° C.).

No. 2a-201

CDCl₃ 300 MHz

0.95(1H, d, J=9.9 Hz), 1.15 and 1.22(each 3H, each s), 1.55-2.60(14H, m), 4.26(1H, m), 5.35-5.63(2H, m), 7.14(1H, d, J=9.9 Hz), 7.34 and 7.40(each, 1H, each d, J=12.9 Hz), 7.62-7.73(4H, m), 8.25-8.30(2H, m), 8.72(1H, d, J=1.5 Hz).

IR(CHCl₃): 3443, 3389, 3297, 3061, 3030, 3016, 2925 2870, 1726, 1708 1652, 1603, 1521, 1483, 1472, 1309/cm.

[α]_(D)=+61.1° (MeOH, c=1.01, 23° C.).

No. 2a-202

CDCl₃ 300 MHz

0.96(1H, d, J=10.2 Hz), 1.09 and 1.22(each 3H, each s), 1.52-2.43(14H, m), 2.63(3H, s), 4.25(1H, m), 5.33-5.49(2H, m), 6.19(1H, d, J=8.4 Hz), 7.10 and 7.58 (each, 2H, each d, J=9.0 Hz), 7.21(1H, m), 7.30-7.32(2H, m), 7.46(1H, d, J=7.5 Hz)

IR(CHCl₃): 3511, 3453, 3062, 3032, 3014, 2925 2870, 1739, 1708, 1650, 1595, 1556, 1516, 1482, 1471/cm.

[α]_(D)=+60.2° (MeOH, c=1.01, 25° C.).

No. 2a-203

CDCl₃ 300 MHz

0.96(1H, d, J=10.5 Hz), 1.09 and 1.23(each 3H, each s), 1.52-2.43(14H, m), 4.23(1H, m), 5.35-5.51(2H, m), 5.93(1H, d, J=8.7 Hz), 6.56(1H, dd, J=0.9 and 1.8 Hz), 7.43(1H, t, J=1.8 Hz), 7.92(1H, dd, J=0.9 and 1.8 Hz).

IR(CHCl₃): 3517, 3450, 3134, 3031, 3008, 2925, 2870, 2667, 1708, 1656, 1588, 1570, 1514/cm.

[α]_(D)=+46.7° (MeOH, c=0.92, 25° C.).

No. 2b-1

[α]_(D)=+25.6° (MeOH, c=1.01, 23° C.).

No. 2b-2

[α]_(D)=+38.9° (MeOH, c=1.01, 24° C.).

No. 2c-1

[α]_(D)=+60.5° (MeOH, c=1.01, 22° C.).

No. 2c-2

[α]_(D)=+55,8° (MeOH, c=0.92, 22° C.).

No. 2c-3

[α]_(D)=+54,7° (MeOH, c=1.01, 22° C.).

No. 2d-1

[α]_(D)=−6.2° (MeOH, c=1.00, 21° C.).

No. 2d-2

[α]_(D)=+15.8° (MeOH, c=0.34, 22° C.).

No. 2d-3

[α]_(D)=+31.6° (MeOH, c=1.01, 22° C.).

No. 2e-1

[α]_(D)=−9.4° (MeOH, c=1.00, 22° C.).

No. 2e-2

[α]_(D)=−1.8° (MeOH, c=1.02, 23° C.).

No. 2e-3

[α]_(D)=−6.7° (MeOH, c=1.01, 23° C.).

No. 2f-1

[α]_(D)=+6.8° (MeOH, c=1.01, 23° C.).

No. 2f-2

[α]_(D)=−2.6° (MeOH, c=1.00, 22° C.).

No. 2f-3

[α]_(D)=−3.6° (MeOH, c=1.01, 22° C.).

No. 2g-1

[α]_(D)=+54,6° (MeOH, c=1.01, 24° C.).

No. 3a-2

CDCl₃ 300 MHz

0.98-2.15(14H, m), 2.31(2H, t, J=7.2 Hz), 2.35-2.40(1H, m), 3.10-3.20(1H, m), 5.00(1H, d, J=6.9 Hz), 5.30-5.48(2H, m), 6.75(1H, d, J=10.2 Hz), 7.38-7.52(6H, m).

IR(CDCl₃): 3266, 3028, 2954, 2874, 1709, 1620, 1448, 1412, 1318, 1141, 970, 892/cm.

[α]_(D)=+20.3±0.6° (CHCl₃, c=1.05, 24° C.).

No. 3a-3

CDCl₃ 300 MHz

0.95-2.00(14H, m), 2.20-2.29(3H, m), 3.00-3.08(1H, m), 3.66(3H, s), 5.00(1H, d J=6.6 Hz), 5.13-5.29(2H, m), 7.38-7.52(3H, m), 7.59-7.65(2H, m), 7.69-7.75(2H, m), 7.92-7.98(2H, m).

IR(CHCl₃): 3376, 3018, 2946, 2868, 1727, 1594, 1436, 1395, 1322, 1157, 1095, 890/cm.

[α]_(D)=+2.3±0.4° (CHCl₃, c=1.03, 22° C.).

mp. 65-66.5° C.

No. 3a-4

CDCl₃ 300 MHz

0.93-2.05(14H, m), 2.15-2.22(1H, m), 2.31(2H, t, J=7.2 Hz), 3.01-3.10(1H, m), 5.18-5.31(3H, m), 7.38-7.52(3H, m), 7.58-7.66(2H, m), 7.69-7.76(2H, m), 7.92-7.98(2H, m)

IR(CHCl₃): 3374, 3260, 3020, 2948, 2868, 1708, 1594, 1479, 1396, 1319, 1156, 1095, 1052, 891/cm.

[α]_(D)=+13.1±0.5° (CHCl₃, c=1.16, 24° C.).

No. 3a-6

CD₃OD 300 MHz

1.04-1.95(14H, m), 2.07(2H, t, J=7.8 Hz), 2.14-2.22(1H, m), 2.94-3.00(1H, m), 5.04-5.25(2H, m), 7.36-7.52(3H, m), 7.66-7.71(2H, m), 7.78-7.85(2H, m), 7.91-7.97(2H, m).

IR(KBr): 3421, 3278, 2951, 2872, 1562, 1481, 1409, 1317, 1156, 1097, 1057, 895/cm

[α]_(D)=−15.3±0.5° (CHCl₃, c=1.06, 23° C.).

mp. 105-112° C.

No. 3a-11

CDCl₃ 300 MHz

0.90-2.04(14H, m), 2.08-2.19(1H, m), 2.35(2H, t, J=7.2 Hz), 2.95-3.04(1H, m), 5.17-5.32(3H, m), 7.56-7.63(2H, m), 7.83-7.95(2H, m).

IR(CHCl₃): 3260, 3020, 2948, 2868, 1707, 1569, 1456, 1383, 1325, 1268, 1160, 1088, 1053, 1006, 892/cm.

[α]_(D)=+8.3±0.5° (CHCl₃, c=1.00, 22° C.).

No. 3a-16

CDCl₃ 300 MHz

0.80-1.90(14H, m), 1.98-2.04(1H, m), 2.27(2H, t, J=7.2 Hz), 2.88(6H, s), 2.90-2.98(1H, m), 4.88-5.00(2H, m), 5.13(1H, d, J=7.2 Hz), 7.18(1H, d,J=7.5 Hz), 7.48-7.60(2H, m), 8.25-8.33(2H, m), 8.53(1H, d, J=8.7 Hz).

IR(CHCl₃): 3272, 3020, 2946, 2866, 2782, 1708, 1573, 1455, 1407, 1311, 1229, 1160, 1142, 1070, 942, 891/cm.

[α]_(D)=−19.7±0.6° (CHCl₃, c=1.08, 23.5° C.).

No. 3a-31

CDCl₃ 300 MHz

0.80-1.85(14H, m), 2.02-2.08(1H, m), 2.20(2H, t, J=7.2 Hz), 2.85-2.95(1H, m), 3.68(3H, s), 4.80-4.92(2H, m), 4.96(1H, d, J=6.9 Hz), 7.50-7.70(3H, m), 7.92-7.98(1H, m), 8.07(1H, d, J=8.4 Hz), 8.29(1H, dd, J=1.5&7.5 Hz), 8.65(1H, d, J=8.7 Hz).

IR(CHCl₃): 3374, 3016, 2946, 2868, 1727, 1506, 1435, 1318, 1160, 1133, 1105, 1051, 984, 890/cm.

[α]_(D)=−39.3±0.8° (CHCl₃, c=1.07, 22° C.).

No. 3a-32

CDCl₃ 300 MHz

0.80-1.90(14H, m), 1.95-2.05(1H, m), 2.27(2H, t, J=7.2 Hz), 2.90-2.96(1, m), 4.85-5.00(2H, m), 5.23(1H, d, J=6.6 Hz), 7.50-7.72(3H, m), 7.95(1H, d, J=8.7 Hz), 8.07(1H, d, J=8.4 Hz), 8.29(1H, dd, J=1.2&7.5 Hz), 8.66(1H, d, J=9.0 Hz).

IR(CHCl₃): 3270, 3020, 2948, 2868, 1708, 1455, 1412, 1317, 1159, 1132, 1104, 1079, 1051, 983, 891/cm.

[α]_(D)=−29.2±0.6° (CHCl₃, c=1.08, 22° C.).

No. 3a-33

CD₃OD 300 MHz

0.94-1.84(14H, m), 1.96-2.08(3H, m), 2.77-2.84(1H, m), 4.67-4.84(2H, m), 7.55-7.75(3H, m), 8.02(1H, d, J=7.8 Hz), 8.12-8.26(2H, m),8.74(1H, d, J=8.7 Hz).

IR(KBr): 3432, 3298, 2951, 2872, 1564, 1412, 1315, 1159, 1134, 1107, 1082, 1058, 986/cm.

[α]_(D)=−79.9±1.2° (CH₃OH, c=1.00, 23° C.).

No. 3a-34

CDCl₃ 300 MHz

0.97-1.91(14H, m), 2.13-2.20(1H, m), 2.42(2H, t, J=7.2 Hz), 3.00-3.07(1H, m), 5.06-5.24(2H, m), 5.33(1H, d, J=6.9 Hz), 7.57-7.68(2H, m), 7.82-8.00(4H, m), 8.45(1H, d, J=1.2 Hz)

IR(CHCl₃): 3260, 3020, 2948, 1708, 1408, 1319, 1154, 1129, 1073, 953, 893/cm.

[α]_(D)=+20.7±0.6° (CHCl₃, c=1.07, 22° C.).

No. 3a-35

CD₃OD 300 MHz

1.03-2.20(m, 17H), 2.97(m, 1H), 5.02(m, 2H), 7.64(m, 2H), 8.00(m, 4H), 8.43(S, 1H).

IR(KBr): 3360, 3285, 1562, 1407, 1316, 1153, 1130, 1075/cm.

[α]_(D)≈0

[α]₃₆₅=+20.9±0.6° (CH₃OH, c=1.04, 23° C.).

No. 3d-1

CDCl₃ 300 MHz

0.93-2.55(m, 17H), 3.02(m, 1H), 5.24(m, 2H), 6.48(m, 1H), 7.35-7.60(m, 3H), 7.85 -8.00(m, 2H)

IR(Nujol): 3275, 1548, 1160, 1094, 758, 719, 689, 591, 557/cm.

[α]_(D)=+19.0±0.6° (CH₃OH, c=1.010, 26.5° C.).

Elemental analysis (C₂₀H₂₆NO₄S 1/2Ca 1.0 H₂O)

Calcd.: C, 57.94; H, 6.82; N, 3.38; Ca, 4.83; H₂O, 4.35

Found: C, 57.80; H, 6.68; N, 3.68; Ca, 5.06; H₂O, 4.50

No. 3d-6

[α]_(D)=−20.7±0.6° (CHCl₃, c=1.00, 24° C.).

No. 3d-7

[α]_(D)=−3.2±0.4° (CHCl₃:c=1.03, 22° C.).

mp. 65-67° C.

No. 3d-8

[α]_(D)=−14.5±0.5° (CHCl₃, c=1.07, 24° C.).

No. 3d-9

[α]_(D)=+12.2±0.5° (CH₃OH, c=1.00, 23° C.).

mp. 119-125° C.

No. 3d-10

[α]_(D)=+39.7±0.8° (CHCl₃, c=1.07, 22° C.).

No. 3d-11

[α]_(D)=+29.2±0.7° (CHCl₃, c=1.06, 22° C.).

No. 3d-12

[α]_(D)=+76.4±1.1° (CH₃OH, c=1.03, 24° C.).

No. 3d-14

[α]_(D)=−20.6±0.6° (CHCl₃, c=1.07, 22° C.).

No. 3d-15

[α]₃₆₅=−28.0±0.7° (CH₃OH, c=1.03, 24.5° C.).

No. 3d-16

[α]_(D)=−8.7±0.5° (CHCl₃, c=1.06, 22° C.).

No. 3d-17

CDCl₃ 300 MHz

0.80-2.15(m, 24H), 2.32(t, J=7 Hz ,2H), 2.68(t, J=7 Hz, 2H), 3.02(m, 1H),2.15(m, 24H), 2.32(t, J=7 Hz, 2H), 2.68(t, J=7 Hz, 2H), 3.02(m, 1H), 5.22(m, 2H), 5.38(d, J=7 Hz, 1H), 7.30(A2B2q-Apart, J=8 Hz, 2H), 7.81(A2B2qBpart, J=8 Hz, 2H), 9.86 (brs, 1H).

[α]_(D)≈0

[α]₃₆₅=−9.7±0.5° (CHCl₃, c=1.03, 22° C.).

No. 3d-24

[α]_(D)=+19.2±0.6° (CHCl₃, c=1.05, 23° C.).

No. 3d-26

CD₃OD 300 MHz

0.90-2.20(20H, m), 2.88(1H, m), 3.07(2H, q, J=7.0 Hz), 5.00-5.40(2H, m), 7.20-7.60(4H, m), 7.95(1H, m).

IR(KBr): 3415, 3254, 1698, 1564, 1314, 1154/cm.

No. 3d-28

CD₃OD 300 MHz

0.90-2.20(20H, m), 2.73(2H, q, J=7.0 Hz), 2.93(1H, m), 5.00-5.30(2H, m), 7.40-7.50(2H, m), 7.60-7.77(2H, m).

IR(KBr): 3435, 3280, 1562, 1323, 1304, 1151/cm.

No. 3d-30

Elemental analysis (C₂₀H₂₅BrNO₄SNa)

Calcd.: C50.21; H5.27; Brl6.70; N2.93; S6.70; Na4.81

Found: C50.22; H5.40; Brl5.57; N2.88; S6.41; Na5.10

IR(KBr): 3425, 3280, 3085, 1697, 1570, 1410, 1321, 1165, 1155/cm.

No. 3e-1

CD₃OD 300 MHz

0.71(1H, d, J=10.2 Hz), 1.04(3H, s), 1.12(3H, s), 1.35-2.28(14H, m), 2.42(3H, s), 3.17-3.25(1H, m), 5.18-5.39(2H, m), 7.37(2H, d, J=8.4 Hz), 7.75(2H, d, J=8.4 Hz).

IR(CHCl₃): 3400, 3289, 2986, 2924, 2870, 1559, 1424, 1322, 1305, 1160, 1095, 1075, 1030/cm.

[α]_(D)=+25.9±0.7° (CH₃OH, c=1.00, 23° C.).

Compounds prepared in Examples above were tested for the in vivo and in vitro activity according to the method shown in Experimental examples below.

EXPERIMENT 1 Binding to PGD₂ Receptor Material and Method

(1) Preparation of Human Platelet Membrane Fraction

Blood sample was obtained using a plastic syringe containing 3.8% sodium citrate from a venous of healthy volunteers (adult male and female), put into a plastic test tube and mixed gently by inversion. The sample was then centrifuged at 1800 rpm, 10 min at room temperature, and supernatant containing PRP (platelet rich plasma) was collected. The PRP was re-centrifuged at 2300 rpm, 22 min at room temperature to obtain platelets. The platelets were homogenized using a homogenizer (Ultra-Turrax) followed by centrifugation 3 times at 20,000 rpm, 10 min at 4° C. to obtain platelet membrane fraction. After protein determination, the membrane fraction was adjusted to 2 mg/ml and preserved in a refrigerator at −80° C. until use.

(2) Binding to PGD₂ Receptor

To a binding-reaction solution (50 mM Tris/HCl, pH 7.4, 5 mM MgCl₂) (0.2 ml) were added human platelet membrane fraction (0.1 mg) and 5 nM [³H]PGD₂ (115Ci/mmol), and reacted at 4° C. for 90 min. After the reaction completed, the reaction mixture was filtered through the glass fiber filter paper, washed several times with cooled saline, and measured radioactivity retained on the filter paper. The specific binding was calculated by subtracting the non-specific binding (the binding in the presence of 10 μM PGD₂) from the total binding. The binding-inhibitory activity of each compound was expressed as concentration required for 50% inhibition (IC₅₀), which was determined by depicting a substitution curve by plotting the binding ratio (%) in the presence of each compound, where the binding ratio in the absence of a test compound is 100%. The results are shown in Table below.

Compound number Activity (μM) compound number activity (μM) 3a-4 0.6 2a-4 0.54 1a-115 8.6 2a-17 0.12 1a-28 0.045 2a-21 5.2 1a-47 0.0086 2a-28 0.046 1a-100 0.56 2a-95 1.6 1a-176 0.047 2a-109 0.003 1a-2 0.13 1a-162 0.027

EXPERIMENT 2 Evaluation of Antagonistic Activity Against PGD₂ Receptor Using Human Platelet

Peripheral blood was obtained from a healthy volunteer using a syringe in which 1/9 volume of citric acid/dextrose solution has been previously added. The syringe was subjected to centrifugation at 180 g for 10 min to obtain the supernatant (PRP: platelet rich plasma). The resultant RRP was washed 3 times with a washing buffer and the number of platelet was counted with a micro cell counter. A suspension adjusted to contain platelet at a final concentration of 5×10⁸/ml was warmed at 37° C., and then subjected to the pre-treatment with 3-isobutyl-1-methylxanthine (0.5 mM) for 5 min. To the suspension was added a test compound diluted at various concentration. Ten-minute later, the reaction was induced by the addition of 0.1-2.0 VM PGD₂ and, 15-minute later, stopped by the addition of HCl. The platelet was destroyed with an ultrasonic homogenizer. After centrifugation, the cAMP in the supernatant was determined by radioassay. PGD₂ receptor antagonism of a drug was evaluated as follows. The inhibition rate regarding cAMP increased by the addition of PGD₂ was determined at individual concentration, and then the concentration of the drug required for 50% inhibition (IC₅₀) was calculated. The results are shown in Table below.

Inhibition of Increase of Compound number Human Platelet cAMP (IC₅₀)(μM) 3a-16 0.37 1a-12 12.11 1a-28 0.30 1a-47 2.09 2a-2 0.77 2a-4 0.94 2a-35 1.52 2a-75 0.71

EXPERIMENT 3 Experiment Using Nasal Occlusion Model

The method used for measuring the nasal cavity resistance and evaluating the anti-nasal occlusion using a guinea pig are described below.

A 1% ovalbumin (OVA) solution was treated with ultrasonic nebulizer to obtain an aerosol. Hartley male guinea pig was sensitized by inhaling twice the aerosol for 10 min at one-week interval. Seven-day after the sensitization, the guinea pig was exposed to an antigen to initiate the reaction. Then the trachea was incised under the anesthesia with pentobarbital (30 mg/kg, i.p.) and cannulas were inserted into the trachea at the pulmonary and nasal cavity sides. The canal inserted at the pulmonary side was connected with an artificial respirator that provides 4 ml air 60 times/min. After arresting the spontaneous respiration of a guinea pig with Garamin (2 mg/kg, i.v.), air was supplied to the snout side with an artificial respirator at the frequency of 70 times/min, and the flow rate of 4 ml air/time, and the atmospheric pressure required for the aeration was measured by the use of a transducer fitted at the branch. The measurement was used as a parameter of the nasal cavity resistance. The exposure of an antigen was carried out by generating aerosol of 3% OVA solution for 3 min between the respirator and nasal cavity cannula. The test drug was injected intravenously 10 min before the antigen exposure. The nasal resistance between 0 to 30 min was measured continuously and the effect was expressed as inhibition rate to that obtained for vehicle using the AUC for 30 min (on the vertical axis, nasal cavity resistance (cm H₂O), and on the horizontal axis, time (0-30 min)) as an indication. The result is shown below.

Compound Inhibition Rate (%) number 1 mg/kg (i.v.) Remarks 1a-28  44 1a-98  69 1a-100 50 1a-115 66 1a-116 48 1a-120 58 3 mg/kg (i.v.) 1a-2  82 1a-162 80 1a-176 60 1a-267 62 2a-4  60 2a-21  52 2a-28  54 2a-95  77 2a-96  77 10 mg/kg (p.o.) 2a-109 73 2a-110 66 10 mg/kg (p.o.) 22a-194  79

Formulation 1

Preparation of Tablets

Tablets each containing 40 mg of active ingredient were prepared in a conventional manner. The ingredients for 40 mg tablet are as follows:

Calcium (+)-(Z)-7-[(1R,2S,3S,4S)-3-benzenesulfonamidobi- 40.0 mg  cyclo[2.2.1]hept-2-yl]-5-heptenoate dihydrate Hydroxypropyl cellulose 3.6 mg  Magnesium stearate 0.4 mg  Cornstarch 18.0 mg  Lactose 58.0 mg  Total 120.0 mg 

Formulation 2

Preparation of Granules

Ingredients:

Calcium (+)-(Z)-7-[(1R,2S,3S,4S)-3-benzenesulfonamidobi- 100.0 mg  cyclo[2.2.1]hept-2-yl]-5-heptenoate dihydrate Hydroxypropyl cellulose 30.0 mg  Carmellose Calcium 30.0 mg  Talc 10.0 mg  Poloxamer 188 20.0 mg  Crystalline cellulose 70.0 mg  Cornstarch 300.0 mg  Lactose 440.0 mg  Total 1000.0 mg  

What is claimed is:
 1. A method for treating a PGD₂-mediated disease selected from the group consisting of systemic mastocytosis, disorder of systemic mast cell activation, allergic rhinitis, allergic conjunctivitis, uticaria, injury due to ischemic reperfusion and nasal occlusion, comprising administering to a subject in need thereof, a PGD₂ antagonist comprising a compound of the general formula (I) below or its salt or hydrate thereof as an active ingredient:

wherein

is A is alkylene which optionally is intervened by hetero atom or phenylene, contains oxo group, and/or has an unsaturated bond; B is hydrogen, alkyl, aralkyl or acyl; R is COOR₁, CH₂OR₂ or CON(R₃)R₄; R₁ is hydrogen or alkyl; R₂ is hydrogen or alkyl; R₃ and R₄ each are independently hydrogen, alkyl, hydroxy or alkylsulphonyl; X₁ is a single bond, phenylene, naphtylene, thiophenediyl, indolediyl, oxazolediyl; X₂ is a single bond, —N═N—, —N═CH—, —CH═N—, —CH═N—N—, —CH═N—O—, —C═NNHCSNH—, —C═NNHCONH—, —CH═CH—, —CH(OH)—, —C(Cl)═C(Cl)—, —(CH₂)n—, ethynylene, —N(R₅)—, —N(R₅₁)CO—, —N(R₅₂)SO₂—, —N(R₅₃)CON(R₅₄)—, —CON(R₅₅)—, —SO₂N(R₅₆)—, O—, —SO—, —SO₂—, —CO—, oxadiazolediyl, thiadiazolediyl, tetrazolediyl; X₃ is alkyl, alkenyl, alkynyl, aryl, aralkyl, heterocyclic group, cycloalkyl, cycloalkenyl, thiazolinylidenemethyl, thiazolidinylidenemethyl, —CH═NR₆ or —N═C(R₇)R₈; R₅, R₅₁, R₅₂, R₅₃, R₅₄, R₅₅ and R₅₆, each are hydrogen or alkyl; R₆ is hydrogen, alkyl, hydroxy, alkoxy, or carbamoyloxy, thiocarbamoyloxy, ureido or thioureido; R₇ and R₈ each are independently alkyl, alkoxy, or aryl; n is 1 or 2; Z is —SO₂— or —CO—; and M is 0 or 1; wherein a cyclic substituent may have one to three substituents selected from the group consisting of nitro, alkoxy, sulfamoyl, substituted- or unsubstituted-amino, acyl, acyloxy, hydroxy, halogen, alkyl, alkynyl, carboxy, alkoxycarbonyl, aralkoxycarbonyl, aryloxycarbonyl, mesyloxy, cyano, alkenyloxy, hydroxyalkyl, trifluoromethyl, alkylthio, —N═PPh₃, oxo, thioxo, hydroxyimino, alkoxyimino, phenyl and alkylenedioxy.
 2. A method according to claim 1, wherein the active ingredient is a compound of the formula (I) wherein

m is 0; Z is SO₂, both X₁ and X₂ are a single bond; X₃ is alkyl, phenyl, naphthyl, stylyl, quinolyl or thienyl; and a cyclic substituent amoung these substituents optionally has one to three substituents selected from a group consisting of nitro, alkoxy, substituted- or unsubstituted-amino, halogen, alkyl and hydroxyalkyl, or its salt or hydrate thereof.
 3. A method according to claim 1, wherein the active ingredient is a compound of the formula (I) wherein

m is 1, both X₁ and X₂ are a single bond; and X₃ is phenyl optionally substituted with halogen, or its salt or hydrate thereof.
 4. A method according to claim 1, wherein the active ingredient is a compound of the formula (I) wherein

m is 1, X₁ is phenylene, X₂ is —CH₂— or —N═N— and X₃ is phenyl, or its salt or hydrate thereof.
 5. A method according to claim 1, wherein the active ingredient is a compound of the formula (I) wherein

p m is 0; and wherein Z is —CO—.
 6. A method according to claim 1, wherein the active ingredient is a compound of the formula (I) wherein

wherein m is
 0. 